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DOI: 10.1055/a-1755-4700
Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines
This work was supported by the National Natural Science Foundation of China (21962004), Jiangxi Provincial Department of Science and Technology (20192BAB203004), and the Fundamental Research Funds for Gannan Medical University (QD201810, TD2021YX05) for financial support.
Abstract
An efficient iridium-catalyzed acceptorless dehydrogenative coupling (ADC) reaction for the preparation of various quinazolines from 2-aminoarylmethanols and amides or nitriles had been developed. A wide range of substituted 2-aminobenzyl alcohols and (hetero)aryl or alkyl benzamides and nitriles were well compatible to afford various quinazolines in excellent yields. Merits of this new strategy are the high atom-economy, mild reaction conditions, and simple operation, and the methodology is suitable for a variety of substrates.
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Substituted quinazolines are kinds of fused heterocycles, which widely exist in numerous alkaloids, natural products, and functional biological molecules (Figure [1]).[1] [2] [3] [4] Due to the great importance of these scaffolds, the development of effective synthetic strategies to access diverse quinazoline derivatives is still desirable.[5]
Up to now, various synthetic strategies for the construction of quinazoline derivatives have been developed.[6] Typical methods can be generalized as the oxidative condensation or oxidative coupling. For instance, contributions for the construction of quinazolines via such strategies include: (i) Oxidative condensation of o-aminobenzophenones,[7] o-aminoarylmethanols,[8] as well as o-haloarylcarbonyl equivalents[9] with benzylic amines, nitriles, oxime ether, and amidines; (ii) Oxidative condensation of o-aminobenzylamines[10] with aldehydes, alcohols, or carboxylic acids; (iii) Oxidative condensation of arylamidines[11] with aldehydes, alcohols, and alkynes; (iv) Oxidative coupling of amidines with o-halobenzylamines[12] and o-halobenzyl halides.[13] Despite great advances in oxidative condensation or oxidative coupling, these synthetic methods still have some defects, such as the use of equivalent or excess amounts of strong oxidants, low atom-economy and prefunctionalized substrates.[14] In this regard, it is highly desirable to develop efficient and environmentally benign methodologies to access quinazoline molecules.
The ADC (acceptorless dehydrogenative coupling) reaction is regarded as atom-economic and environment friendly method for the construction of quinazolines (Scheme [1]).[15] Great achievements had been furnished in this content. For instance, the groups of Balaraman (Scheme [1a])[16] and Srimani (Scheme [1b]) [17] reported a manganese-catalyzed ADC reaction of amines for direct synthesis of N-heterocycles with alcohols. Meanwhile, Ru-catalyzed (Scheme [1a] and 1c),[18] iridium-catalyzed (Scheme [1b]),[19] and Ni-catalyzed (Scheme [1a])[20] ADC reaction were also explored for the synthesis of quinazolines. In addition, the cheap metal such as Fe was also served as catalyst for the ADC reaction to construct quinazolines.[21] Nevertheless, due to the harsh reaction conditions (such as the reaction temperature was up to 130 °C) and the need of high efficiency catalytic system to meet with the sustainable development, there is still room for improvement in the ADC reaction.
Recently, we have developed a series of transfer hydrogenation and borrowing hydrogenation transformation via iridium catalysts.[22] Encouraged and inspired by these progresses, we supposed that these cyclometalated iridium complexes could be also employed for the ADC reaction. Herein, we display a general and efficient method for the constructions of quinazolines from 2-aminoarylmethanols and benzamides or nitriles via sequential dehydrogenative annulation and N-alkylation reaction by using cyclometalated iridium complexes, which is featured with high atom-economy, low reaction temperature, broad substrate scope, and high efficiency (Scheme [1d]).
2-Aminobenzyl alcohol (1a) and benzamide (2a) were chosen for our initial studies to explore this iridium-catalyzed ADC reaction. Typical conditions, including iridium catalysts, solvents, bases, as well as temperatures were tested. Satisfactorily, the desired 71% yield of 3aa, albeit with 29% yield of 4aa (which might be formed via transfer hydrogenation of 3aa) was formed by using toluene as solvent, t-BuOK as base and TC-1 as catalyst at 100 °C in the air (Table [1], entry 1). Tang’s catalyst (TC) screening showed that TC-6 was the optimal catalyst, delivering the highest 98% yield of 3aa (entries 1–6). Control experiment displayed no corresponding product of 3aa was achieved in the absence of iridium catalyst, which indicated the necessity of iridium catalyst (entry 8). Corresponding base screening including t-BuONa, CH3CO2K, HCO2Na, NaOH and KOH (entries 8–14) under the standard conditions evidenced the t-BuOK as the optimal base. Besides, solvent screening displayed the importance of the reaction media. For example, 75%, 99%, 89%, 62%, or 71% yield was obtained by employing xylene, 1,4-dioxane, THF, DMF, or H2O as solvent, respectively (entries 15–19). It is worth noting that almost the same high yield of 3aa was provided even at lower reaction temperature of 80 °C under the standard conditions (entry 20). However, longer time was needed to furnish this transformation when further decrease of reaction temperature to 60 °C was applied (entry 21).
a Reaction conditions: a mixture of 1a (1.0 mmol), 2a (1.1 mmol), base (1.1 mmol), solvent (2.0 mL), and Tang’s catalyst (TC, 0.1 mol%) at 100 °C in the air for 12 h.
b Determined by GC-MS analysis.
c Catalyst: 0.01 mol% was used for 48 h.
d No Tang’s catalyst was used for 36 h.
e Reaction time: 8 h.
f Reaction temperature: 80 °C.
g Conditions: 80 °C for 12 h.
h Conditions: 60 °C for 36 h.
With the optimized conditions in hand, we set out to investigate the substrate scope and compatibility of this iridium-catalyzed ADC reaction for the synthesis of quinazolines (Scheme [2]). In general, o-aminobenzyl alcohols could react with various substituted amides, respectively, under the optimized reaction conditions to give the products in excellent yields. On the other hand, miscellaneous benzamides bearing both electron-donating and electron-withdrawing groups were well tolerated in this catalytic system, affording the corresponding quinazolines in excellent yields (87–95%). For instance, substrates bearing strong electron-withdrawing group such as CF3 and strong electron-donating group such as OCH3 were well compatible with this iridium-catalyzed ADC reaction system. Interestingly, the positions of the substituted groups had slight influence on the yields of the products. For example, the small steric hinderance meta- and para-substituted substrates of benzamides gave excellent yields of the ADC products, such as 3ac–ae, 3ag–aj, 3bd–bg, and 3cd–ch. Obviously, the ortho-substituted substrates also delivered the corresponding products 3ab, 3af, 3bb, and 3cb in excellent yields, which showcased the high efficiency of this iridium-catalyzed ADC reaction of o-aminoarylmethanols bearing huge steric hindrance. Furthermore, the 1-naphthamide which contains a fused-ring could also afford the target product 3ak in 95% yield. To expand the substrate scope of this catalytic system, iridium-catalyzed ADC reactions of heteroaromatic amides was also investigated. For instance, 2-thiophenecarboxamide (2l), which contains aromatic heterocycle could also be utilized as substrate, giving 3al in 95% yield. Most importantly, the 2-alkyl-substituted quinazoline 3ap was generated by employing the alkyl-substituted amide 2p as the reaction substrate, which showed promising application in organic synthesis. It is worth noting that full conversion was also accomplished when tertiary amide (2,2,2-trimethylacetamide) was employed in this catalytic system. Nevertheless, we could not obtain the corresponding pure product by column chromatography.
Next, the iridium-catalyzed ADC reaction of o-aminobenzyl alcohols with nitriles was also investigated to explore the substrate scope to afford quinazolines (Table [2]). To our delight, 96% yield of 3aa was obtained with benzonitrile as coupling reagent under the pre-optimized reaction conditions of o-aminobenzyl alcohols with amides (Table [2], entry 1). To achieve the optimal conditions, more reaction parameters were investigated. For example, simple bases (entries 2–7) and solvents screening (entries 8–12) found that 1,4-dioxane was the best solvent and KOH was the most suitable base, respectively. Satisfactorily, almost the same excellent yield of 3aa was also provided when catalyst amount was decreased to 0.01 mol% just by extending the reaction time (entry 13).
a Reaction conditions: a mixture of 1a (1.0 mmol), 5a (1.1 mmol), base (1.1 mmol), solvent (2.0 mL), and TC-6 (0.1 mol%) at 100 °C in the air for 16 h.
b Determined by GC-MS analysis.
c Reaction time: 8 h.
d TC-6 used: 0.01 mol% for 48 h.
Based on the optimal conditions of iridium-catalyzed ADC reaction of o-aminobenzyl alcohols with benzonitriles, the substrate scope of o-aminoarylmethanols and nitriles was studied, which also revealed that both electronic effect and steric hindrance had slight influence on yields (Scheme [3]). For example, methyl-, fluoro-, and chloro-substituted benzonitriles were readily coupled with o-aminoarylmethanols to deliver the corresponding products 3 in superior yields. Obviously, naphthyl nitrile, which contains a fused-ring regarded as bulky group also produced 3ak in 90% yield. Reaction of heteroaromatic nitriles, such as 2-thiophenecarbonitrile was explored, which also worked well to deliver quinazoline 3al in excellent yield. In addition, alkyl nitriles were found to be well compatible in this the reaction to provide the product of 3ap in 91% yield.
In order to demonstrate the potential application of this methodology, a gram-scale experiment was conducted with the model reaction (Scheme [4]). A large-scale of 2-aminobenzylalcohol (1a) on 10.0 mmol scale was performed with benzamide (2a) under standard conditions, providing the corresponding product 3aa in 95% yield (1.96 g), which shows the potential applicability of this transformation in organic synthesis.
Based on the experiment results and literature,[22] a plausible mechanism is proposed for this iridium-catalyzed ADC transformation (Scheme [5]). First, the Int-I is formed by the ‘borrowing hydrogen’ process under the interaction of TC-6 with 1,[22a] [e] which undergoes β-H elimination to form Int-II and 2-aminobenzaldehyde (6). In this process, the dehydrogenation of benzyl alcohol to form the amount of liberated H2 was determined by previous literature.[16] [22e] Finally, the condensation and cyclization of 6 with amides provides the desired products 3 under basic condition. It is worth noting that base can also induce nitrile hydration to amides,[8b] [20] which results in the same product 3.
In conclusion, a sustainable and practicable strategy for the synthesis of quinazoline derivatives had been discovered via iridium-catalyzed ADC transformation of o-aminoarylmethanols with amides or nitriles in relatively mild conditions (80 °C), which exhibited wide functional groups compatibility to afford serious of quinazolines under excellent yields, with only H2 and H2O as by-products. Large-scale experiment was also realized via this catalytic system.
All the starting materials and solvents were commercially purchased and used directly without purification. The products were purified by flash column chromatography on silica gel (200–300 mesh). The melting points of the products were determined using WRR melting point apparatus. The 1H NMR and 13C NMR of the products were recorded by 400 MHz NMR spectrometer (CDCl3, δH 7.26, δC 77.23). The process of the reaction and the ratio of the product 3aa and 4aa were detected by Agilent GC-7900.
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Quinazolines 3 from 1 and 2; General Procedure
In a 10.0 mL Schlenk tube, a mixture of 1 (1.0 mmol), 2 (1.1 mmol), t-BuOK (1.1 mmol), 1,4-dioxane (2.0 mL), and TC-6 (0.1 mol%) was reacted at 80 °C in the air. After completion of the reaction, the mixture was extracted with EtOAc (3 × 10 mL). The combined EtOAc layers were then dried (MgSO4) and concentrated in vacuum. The resulting crude product was purified by silica gel chromatography using a mixture of EtOAc/PE (1:20–1:50).
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Quinazolines 3 from 1 and 5; General Procedure
In a 10.0 mL Schlenk tube, a mixture of 1 (1.0 mmol), 5 (1.1 mmol), KOH (1.1 mmol), 1,4-dioxane (2.0 mL), and TC-6 (0.1 mol%) was reacted at 100 °C in the air. After completion of the reaction, the mixture was extracted with EtOAc (3 × 10 mL). The combined EtOAc layers were then dried (MgSO4) and concentrated in vacuum. The resulting crude product was purified by silica gel chromatography using a mixture of EtOAc/PE (1:20–1:50) as eluent.
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Gram-Scale Preparation of 2-Phenylquinazoline (3aa)
In a 100.0 mL Schlenk tube, a mixture of 1a (10.0 mmol), 2a (11.0 mmol), t-BuOK (11.0 mmol), 1,4-dioxane (20.0 mL), and TC-6 (0.1 mol%) was reacted at 80 °C in the air. After completion of the reaction, the mixture was extracted with EtOAc (3 × 50.0 mL). The combined EtOAc layers were then dried (MgSO4) and concentrated in vacuum. The resulting crude product was purified by silica gel chromatography using a mixture of EtOAc/PE (1:20) as eluent.
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2-Phenylquinazoline (3aa)[8a]
Yellow solid; mp 99–100 °C; yield: 195.8 mg (95%).
1H NMR (400 MHz, CDCl3): δ = 9.49 (d, J = 0.8 Hz, 1 H), 8.62 (dd, J = 7.9, 1.8 Hz, 2 H), 8.11 (d, J = 8.5 Hz, 1 H), 7.97–7.89 (m, 2 H), 7.66–7.59 (m, 1 H), 7.54 (d, J = 7.7 Hz, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.06, 160.55, 150.77, 137.99, 134.20, 130.67, 128.68, 128.65, 128.61, 127.34, 127.17, 123.62.
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2-o-Tolylquinazoline (3ab)[8a]
Yellow solid; mp 44–47 °C; yield: 198.1 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 9.49 (s, 1 H), 8.09 (d, J = 8.4 Hz, 1 H), 7.95–7.85 (m, 3 H), 7.63 (t, J = 7.6 Hz, 1 H), 7.38–7.29 (m, 3 H), 2.61 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 164.05, 160.12, 150.40, 138.62, 137.41, 134.15, 131.33, 130.69, 129.34, 128.59, 127.55, 127.10, 126.02, 122.93, 21.09.
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2-m-Tolylquinazoline (3ac)[8a]
Yellow oil; yield: 200.3 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.40 (s, 1 H), 8.42 (s, 2 H), 8.05 (d, J = 8.5 Hz, 1 H), 7.84 (s, 2 H), 7.53 (s, 1 H), 7.42 (s, 1 H), 7.31 (s, 1 H), 2.47 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.19, 160.45, 150.76, 138.28, 137.99, 134.09, 131.47, 129.16, 128.62, 128.60, 127.20, 127.13, 125.85, 123.57, 21.60.
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2-p-Tolylquinazoline (3ad)[8a]
Yellow solid; mp 101–102 °C; yield: 202.5 mg (92%).
1H NMR (400 MHz, CDCl3): δ = 9.44 (s, 1 H), 8.51 (d, J = 8.2 Hz, 2 H), 8.07 (d, J = 8.3 Hz, 1 H), 7.90 (t, J = 9.1 Hz, 2 H), 7.62–7.56 (m, 1 H), 7.34 (d, J = 7.9 Hz, 2 H), 2.45 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.15, 160.47, 150.80, 140.92, 135.30, 134.09, 129.44, 128.55, 127.15, 127.07, 123.53, 21.54.
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2-(4-Methoxyphenyl)quinazoline (3ae)[8a]
Yellow solid; mp 83–84 °C; yield: 221.9 mg (94%).
1H NMR (400 MHz, CDCl3): δ = 9.42 (s, 1 H), 8.58 (d, J = 8.9 Hz, 2 H), 8.04 (d, J = 8.3 Hz, 1 H), 7.88 (t, J = 8.6 Hz, 2 H), 7.61–7.54 (m, 1 H), 7.05 (d, J = 8.9 Hz, 2 H), 3.90 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.85, 160.88, 160.44, 150.85, 134.07, 130.72, 130.23, 128.41, 127.16, 126.83, 123.33, 114.00, 55.42.
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2-(2-Trifluoromethylphenyl)quinazoline (3af)[23]
Yellow solid; mp 67–68 °C; yield: 249.4 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.50 (s, 1 H), 8.11 (d, J = 8.4 Hz, 1 H), 8.00–7.91 (m, 2 H), 7.85 (s, 2 H), 7.71–7.63 (m, 2 H), 7.58 (t, J = 7.7 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 162.43, 160.20, 150.18, 138.81, 134.53, 131.67, 129.14, 128.63, 128.15, 127.18, 126.91, 123.28.
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2-(3-Trifluoromethylphenyl)quinazoline (3ag)[23]
Yellow solid; mp 122–123 °C; yield: 252.2 mg (92%).
1H NMR (400 MHz, CDCl3): δ = 9.44 (d, J = 0.8 Hz, 1 H), 8.92 (s, 1 H), 8.80 (d, J = 7.7 Hz, 1 H), 8.08 (d, J = 8.9 Hz, 1 H), 7.94–7.87 (m, 2 H), 7.74 (d, J = 7.0 Hz, 1 H), 7.66–7.59 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 160.62, 159.50, 150.63, 138.81, 134.38, 131.69, 131.68, 129.08, 127.77, 127.17, 127.07, 127.04, 125.51, 125.47, 123.80.
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2-(4-Trifluoromethylphenyl)quinazoline (3ah)[23]
Yellow solid; mp 141–142 °C; yield: 257.7 mg (94%).
1H NMR (400 MHz, CDCl3): δ = 9.39 (s, 1 H), 8.68 (d, J = 8.1 Hz, 2 H), 8.04 (d, J = 8.4 Hz, 1 H), 7.88 (t, J = 7.8 Hz, 2 H), 7.74 (d, J = 8.2 Hz, 2 H), 7.59 (t, J = 7.4 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 160.55, 159.48, 150.57, 141.27, 134.33, 128.80, 128.72, 127.83, 127.12, 125.52, 125.48, 125.44, 123.77.
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2-(3-Chlorophenyl)quinazoline (3ai)[23]
Yellow solid; mp 149–150 °C; yield: 216.4 mg (90%).
1H NMR (400 MHz, CDCl3): δ == 9.43 (s, 1 H), 8.62 (d, J = 1.7 Hz, 1 H), 8.50 (ddd, J = 6.1, 2.6, 1.6 Hz, 1 H), 8.07 (d, J = 8.8 Hz, 1 H), 7.94–7.86 (m, 2 H), 7.65–7.58 (m, 1 H), 7.49–7.41 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 160.57, 159.68, 150.65, 139.87, 134.79, 134.32, 130.55, 129.87, 128.68, 128.66, 127.66, 127.16, 126.66, 123.76.
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2-(4-Chlorophenyl)quinazoline (3aj)[8a]
Yellow solid; mp 129–130 °C; yield: 228.1 mg (95%).
1H NMR (400 MHz, CDCl3): δ = 9.44 (s, 1 H), 8.57 (d, J = 8.7 Hz, 2 H), 8.07 (d, J = 8.4 Hz, 1 H), 7.91 (t, J = 7.7 Hz, 2 H), 7.65–7.59 (m, 1 H), 7.49 (d, J = 8.6 Hz, 2 H).
13C NMR (101 MHz, CDCl3): δ = 160.56, 160.05, 150.70, 136.86, 136.53, 134.30, 129.92, 128.85, 128.61, 127.49, 127.18, 123.63.
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2-(Naphthalen-2-yl)quinazoline (3ak)[8a]
Yellow solid; mp 133–134 °C; yield: 240.7 mg (94%).
1H NMR (400 MHz, CDCl3): δ = 9.52 (s, 1 H), 9.16 (s, 1 H), 8.73 (d, J = 8.5 Hz, 1 H), 8.14 (d, J = 8.4 Hz, 1 H), 7.97 (dd, J = 37.2, 19.0, 8.0 Hz, 5 H), 7.63 (t, J = 7.5 Hz, 1 H), 7.58–7.50 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 161.04, 160.57, 150.86, 135.37, 134.71, 134.24, 133.44, 129.31, 128.99, 128.67, 128.33, 127.75, 127.36, 127.22, 127.14, 126.27, 125.43, 123.66.
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2-(Thiophen-2-yl)quinazoline (3al)[8a]
Yellow solid; mp 130–131 °C; yield: 186.6 mg (88%).
1H NMR (400 MHz, CDCl3): δ = 9.36 (s, 1 H), 8.20–8.13 (m, 1 H), 8.01 (d, J = 8.7 Hz, 1 H), 7.92–7.85 (m, 2 H), 7.61–7.50 (m, 2 H), 7.20 (dd, J = 5.0, 3.7 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 160.58, 157.88, 150.64, 143.83, 134.41, 129.99, 129.27, 128.42, 128.20, 127.31, 127.04, 123.40.
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8-Methyl-2-phenylquinazoline (3ba)[8a]
Yellow solid; mp 52–53 °C; yield: 200.3 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.40 (s, 1 H), 8.66 (dd, J = 8.0, 1.7 Hz, 2 H), 7.75–7.68 (m, 2 H), 7.57–7.43 (m, 4 H), 2.85 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.58, 159.94, 149.73, 138.40, 137.15, 133.87, 130.48, 128.61, 128.54, 126.94, 124.83, 123.52, 16.97.
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8-Methyl-2-o-tolylquinazoline (3bb)[24]
Yellow solid; mp 47–48 °C; yield: 208.3 mg (89%).
1H NMR (400 MHz, CDCl3): δ = 9.44 (s, 1 H), 8.14–8.06 (m, 1 H), 7.74 (t, J = 7.8 Hz, 1 H), 7.53–7.47 (m, 1 H), 7.36 (q, J = 4.8, 4.3 Hz, 3 H), 2.77 (d, J = 29.1 Hz, 6 H).
13C NMR (101 MHz, CDCl3): δ = 162.51, 160.24, 149.41, 138.46, 137.91, 137.14, 133.81, 131.56, 131.15, 129.32, 127.11, 126.00, 124.75, 122.75, 21.93, 17.24.
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8-Methyl-2-p-tolylquinazoline (3bd)[23]
Yellow solid; mp 94–95 °C; yield: 215.4 mg (92%).
1H NMR (400 MHz, CDCl3): δ = 9.36 (s, 1 H), 8.54 (d, J = 8.2 Hz, 2 H), 7.72–7.66 (m, 2 H), 7.42 (t, J = 7.6 Hz, 1 H), 7.32 (d, J = 8.0 Hz, 2 H), 2.82 (s, 3 H), 2.43 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.48, 160.02, 149.73, 140.65, 137.01, 135.71, 133.77, 129.36, 128.48, 126.67, 124.79, 123.39, 21.55, 16.96.
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2-(3-Fluorophenyl)-8-methylquinazoline (3bm)[24]
Yellow solid; mp 116–117 °C; yield: 214.3 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 9.30 (s, 1 H), 8.59 (d, J = 1.9 Hz, 1 H), 8.51–8.46 (m, 1 H), 7.65 (d, J = 7.5 Hz, 2 H), 7.44–7.38 (m, 3 H), 2.78 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.51, 158.44, 149.47, 140.16, 137.14, 134.64, 133.99, 130.32, 129.74, 128.51, 127.25, 126.57, 124.77, 123.59, 16.95.
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2-(4-Fluorophenyl)-8-methylquinazoline (3bn)[24]
Yellow solid; mp 124–125 °C; yield: 221.4 mg (93%).
1H NMR (400 MHz, CDCl3): δ = 9.30 (s, 1 H), 8.58–8.52 (m, 2 H), 7.69–7.63 (m, 2 H), 7.48–7.40 (m, 3 H), 2.78 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.50, 158.82, 149.53, 137.04, 136.82, 136.59, 133.95, 129.79, 128.71, 127.07, 124.79, 123.46, 16.92.
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8-Methyl-2-(3-trifluoromethylphenyl)quinazoline (3bg)[25]
Yellow oil; yield: 262.2 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.44 (s, 1 H), 8.95 (s, 1 H), 8.86 (d, J = 7.8 Hz, 1 H), 7.76 (t, J = 9.8 Hz, 3 H), 7.65 (t, J = 7.8 Hz, 1 H), 7.54 (t, J = 7.6 Hz, 1 H), 2.87 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.75, 158.50, 149.63, 139.17, 137.29, 131.65, 129.05, 127.47, 126.93, 126.89, 125.41, 125.37, 124.89, 123.77, 16.95.
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6-Chloro-2-o-tolylquinazoline (3cb)[25]
Yellow solid; mp 102–103 °C; yield: 228.7 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 9.40 (s, 1 H), 8.02 (d, J = 9.0 Hz, 1 H), 7.96–7.88 (m, 2 H), 7.82 (dd, J = 9.0, 2.4 Hz, 1 H), 7.40–7.29 (m, 3 H), 2.61 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 164.20, 159.12, 148.86, 138.06, 137.60, 135.09, 133.06, 131.46, 130.78, 130.36, 129.60, 126.06, 125.77, 123.30, 21.25.
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6-Chloro-2-p-tolylquinazoline (3cd)[23]
Yellow solid; mp 172–173 °C; yield: 233.8 mg (92%).
1H NMR (400 MHz, CDCl3): δ = 9.33 (s, 1 H), 8.46 (d, J = 8.3 Hz, 2 H), 7.98 (d, J = 9.0 Hz, 1 H), 7.84 (d, J = 2.3 Hz, 1 H), 7.78 (dd, J = 9.0, 2.4 Hz, 1 H), 7.32 (d, J = 8.0 Hz, 2 H), 2.43 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.35, 159.45, 149.26, 141.23, 134.99, 134.87, 132.50, 130.29, 129.48, 128.55, 125.82, 123.88, 21.57.
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6-Chloro-2-(3-methoxyphenyl)quinazoline (3co)[23]
Yellow solid; mp 133–134 °C; yield: 245.8 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.27 (s, 1 H), 8.19–8.09 (m, 2 H), 7.94 (d, J = 8.7 Hz, 1 H), 7.80–7.71 (m, 2 H), 7.41 (t, J = 7.9 Hz, 1 H), 7.04 (d, J = 8.2 Hz, 1 H), 3.91 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.92, 160.00, 159.39, 149.09, 138.97, 134.98, 132.75, 130.35, 129.67, 125.78, 123.96, 121.15, 117.39, 113.06, 55.43.
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6-Chloro-2-(4-methoxyphenyl)quinazoline (3ce)[23]
Yellow solid; mp 165–166 °C; yield: 253.9 mg (94%).
1H NMR (400 MHz, CDCl3): δ = 9.31 (s, 1 H), 8.54 (s, 1 H), 8.52 (s, 1 H), 7.94 (s, 1 H), 7.83 (s, 1 H), 7.76 (d, J = 2.2 Hz, 1 H), 7.04 (s, 1 H), 7.02 (s, 1 H), 3.89 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 162.05, 161.07, 159.41, 149.30, 134.97, 132.21, 130.21 , 125.84, 123.67, 114.03, 55.42.
#
6-Chloro-2-(3-trifluoromethylphenyl)quinazoline (3cg)[18a]
Yellow solid; mp 109–110 °C; yield: 277.2 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 9.28 (s, 1 H), 8.83 (s, 1 H), 8.70 (d, J = 7.8 Hz, 1 H), 7.94 (d, J = 8.9 Hz, 1 H), 7.82–7.70 (m, 3 H), 7.59 (t, J = 7.8 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 159.51, 148.97, 138.25, 135.26, 133.32, 131.61, 131.60, 131.24, 130.36, 129.09, 127.28, 127.24, 125.78.
#
6-Chloro-2-(4-trifluoromethylphenyl)quinazoline (3ch)[18a]
Yellow solid; mp 141–142 °C; yield: 283.4 mg (92%).
1H NMR (400 MHz, CDCl3): δ = 9.39 (s, 1 H), 8.70 (d, J = 8.1 Hz, 2 H), 8.03 (d, J = 8.9 Hz, 1 H), 7.94–7.89 (m, 1 H), 7.85 (dd, J = 9.6, 1.6 Hz, 1 H), 7.77 (d, J = 8.2 Hz, 2 H).
13C NMR (101 MHz, CDCl3): δ = 159.82, 159.64, 149.11, 140.83, 135.40, 133.51, 132.52, 130.49, 128.83, 125.87, 125.59, 125.56, 124.22.
#
6,8-Dibromo-2-p-tolylquinazoline (3dd)[7a]
Yellow solid; mp 129–130 °C; yield: 327.0 mg (87%).
1H NMR (400 MHz, CDCl3): δ = 9.37 (s, 1 H), 8.48 (d, J = 8.2 Hz, 2 H), 8.06 (s, 1 H), 7.94 (d, J = 1.1 Hz, 2 H), 7.34 (d, J = 8.0 Hz, 2 H), 2.44 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.43, 159.34, 149.48, 141.27, 137.54, 134.89, 130.38, 129.49, 129.23, 128.57, 124.40, 120.45, 21.56.
#
6,8-Dibromo-2-(4-methoxyphenyl)quinazoline (3de)[26]
Yellow solid; mp 176–177 °C; yield: 348.8 mg (89%).
1H NMR (400 MHz, CDCl3): δ = 9.30 (d, J = 21.9 Hz, 1 H), 8.59 (dd, J = 32.7, 8.9 Hz, 2 H), 8.07–7.85 (m, 2 H), 7.04 (dd, J = 9.0, 1.9 Hz, 2 H), 3.90 (d, J = 2.0 Hz, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.44, 159.36, 149.49, 141.28, 137.55, 134.90, 130.39, 129.50, 129.24, 128.58, 124.41, 120.47, 21.57.
#
6,8-Dibromo-2-(3-trifluoromethylphenyl)quinazoline (3dg)
Yellow solid; mp 102–103 °C; yield: 391.2 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.41 (s, 1 H), 8.91 (s, 1 H), 8.80 (d, J = 7.8 Hz, 1 H), 8.14–8.09 (m, 1 H), 7.99 (d, J = 1.3 Hz, 2 H), 7.77 (d, J = 7.7 Hz, 1 H), 7.65 (t, J = 7.8 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 159.82, 159.55, 149.33, 138.38, 137.93, 131.70, 131.03, 130.50, 129.30, 129.16, 127.32, 125.55, 125.52, 124.69, 121.37.
#
2-Propylquinazoline (3ap)[8b]
Yellow oil; yield: 160.1 mg (93%).
1H NMR (400 MHz, CDCl3): δ = 9.35 (s, 1 H), 7.98 (d, J = 8.6 Hz, 1 H), 7.88 (t, J = 7.8 Hz, 2 H), 7.60 (t, J = 7.5 Hz, 1 H), 3.14–3.07 (m, 2 H), 1.96 (dd, J = 15.1, 7.5 Hz, 2 H), 1.05 (t, J = 7.4 Hz, 3 H).
13C NMR (101 MHz, CDCl3): δ = 167.68, 160.38, 150.31, 134.01, 127.86, 127.07, 126.93, 123.05, 41.88, 22.34, 14.01.
#
2-(2,3-Dimethylphenyl)quinazoline (3aq)[27]
Yellow solid; mp 66–67 °C; yield: 206.0 mg (88%).
1H NMR (400 MHz, CDCl3): δ = 9.51 (s, 1 H), 8.10 (d, J = 8.4 Hz, 1 H), 8.01–7.90 (m, 2 H), 7.67 (t, J = 7.5 Hz, 1 H), 7.58 (d, J = 6.9 Hz, 1 H), 7.25 (d, J = 8.4 Hz, 2 H), 2.38 (d, J = 3.0 Hz, 6 H).
13C NMR (101 MHz, CDCl3): δ = 164.92, 160.13, 150.37, 139.42, 137.72, 135.20, 134.21, 130.75, 128.57, 128.24, 127.59, 127.11, 125.55, 122.91, 20.61, 16.81.
#
2-(3,4-Dimethylphenyl)quinazoline (3ar)[27]
Yellow solid; mp 73–74 °C; yield: 210.7 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 9.43 (s, 1 H), 8.45–8.30 (m, 2 H), 8.06 (d, J = 8.4 Hz, 1 H), 7.87 (t, J = 8.1 Hz, 2 H), 7.57 (t, J = 7.5 Hz, 1 H), 7.29 (d, J = 7.9 Hz, 1 H), 2.39 (s, 3 H), 2.35 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.30, 160.43, 150.83, 139.64, 136.90, 135.66, 134.05, 130.08, 129.60, 128.54, 127.15, 127.00, 126.17, 123.51, 19.95, 19.90.
#
2-(3,5-Dimethylphenyl)quinazoline (3as)[27]
Yellow solid; mp 93–94 °C; yield: 215.4 mg (92%).
1H NMR (400 MHz, CDCl3): δ = 9.44 (s, 1 H), 8.23 (s, 2 H), 8.08 (d, J = 8.6 Hz, 1 H), 7.88 (t, J = 7.7 Hz, 2 H), 7.57 (t, J = 7.5 Hz, 1 H), 7.14 (s, 1 H), 2.44 (s, 6 H).
13C NMR (101 MHz, CDCl3): δ = 161.38, 160.43, 150.79, 138.24, 137.92, 134.10, 132.44, 128.59, 127.17, 127.14, 126.39, 123.57, 21.46.
#
2-(3-Fluorophenyl)quinazoline (3am)[28]
Yellow solid; mp 99–100 °C; yield: 197.2 mg (88%).
1H NMR (400 MHz, CDCl3): δ = 9.36 (s, 1 H), 8.38 (d, J = 7.8 Hz, 1 H), 8.30 (d, J = 10.3 Hz, 1 H), 8.02 (d, J = 8.4 Hz, 1 H), 7.84 (t, J = 7.9 Hz, 2 H), 7.54 (t, J = 7.5 Hz, 1 H), 7.50–7.40 (m, 1 H), 7.17 (t, J = 8.0 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 164.48, 162.05, 160.48, 150.57, 140.49, 134.23, 130.09, 130.01, 128.64, 127.57, 127.10, 124.21, 123.70, 117.55, 117.33, 115.51, 115.28.
#
2-(Naphthalen-1-yl)quinazoline (3at)[8a]
Yellow solid; mp 123–124 °C; yield: 233.1 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.52 (s, 1 H), 8.72 (d, J = 8.3 Hz, 1 H), 8.16 (dd, J = 18.5, 7.9 Hz, 2 H), 7.96 (d, J = 8.2 Hz, 1 H), 7.94–7.80 (m, 3 H), 7.56 (ddd, J = 30.1, 16.2, 7.6 Hz, 4 H).
13C NMR (101 MHz, CDCl3): δ = 163.46, 160.46, 150.56, 136.37, 134.36, 134.24, 131.29, 130.47, 129.75, 128.64, 128.57, 127.76, 127.18, 126.95, 125.98, 125.38, 123.13.
#
8-Methyl-2-(m-tolyl)quinazoline (3bc)[27]
Yellow solid; mp 57–58 °C; yield: 210.7 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 9.31 (s, 1 H), 8.45 (d, J = 6.3 Hz, 2 H), 7.61 (d, J = 7.6 Hz, 2 H), 7.38 (dt, J = 14.7, 7.6 Hz, 2 H), 7.28 (d, J = 7.6 Hz, 1 H), 2.79 (s, 3 H), 2.46 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.46, 160.02, 149.67, 138.35, 138.16, 137.06, 133.80, 131.31, 129.12, 128.55, 126.82, 125.80, 124.79, 123.45, 21.67, 17.00.
#
2-(3,4-Dimethylphenyl)-8-methylquinazoline (3br)[27]
Yellow solid; mp 127–128 °C; yield: 225.8 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.31 (s, 1 H), 8.38 (d, J = 12.2 Hz, 2 H), 7.62 (d, J = 7.7 Hz, 2 H), 7.36 (t, J = 7.6 Hz, 1 H), 7.26 (d, J = 7.8 Hz, 1 H), 2.80 (s, 3 H), 2.37 (s, 3 H), 2.31 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 160.41, 160.13, 149.73, 139.37, 136.99, 136.73, 136.07, 133.73, 130.01, 129.59, 126.59, 126.15, 124.79, 123.36, 20.02, 19.92, 17.00.
#
2-(3,5-Dimethylphenyl)-8-methylquinazoline (3bs)[27]
Yellow solid; mp 92–93 °C; yield: 230.7 mg (93%).
1H NMR (400 MHz, CDCl3): δ = 9.34 (s, 1 H), 8.26 (s, 2 H), 7.65 (d, J = 7.6 Hz, 2 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.11 (s, 1 H), 2.83 (s, 3 H), 2.44 (s, 6 H).
3C NMR (101 MHz, CDCl3): δ = 160.43, 160.19, 149.72, 138.29, 138.10, 137.09, 133.80, 132.27, 126.77, 126.36, 124.80, 123.44, 21.53, 17.03.
#
6-Chloro-2-(m-tolyl)quinazoline (3cc)[17]
Yellow solid; mp 141–142 °C; yield: 231.2 mg (91%).
1H NMR (400 MHz, CDCl3): δ = 9.35 (s, 1 H), 8.38 (d, J = 9.4 Hz, 2 H), 8.00 (d, J = 9.0 Hz, 1 H), 7.87 (s, 1 H), 7.80 (d, J = 9.1 Hz, 1 H), 7.42 (t, J = 7.6 Hz, 1 H), 7.32 (d, J = 7.6 Hz, 1 H), 2.48 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 161.43, 159.47, 149.24, 138.38, 137.51, 135.07, 132.72, 131.73, 130.35, 129.13, 128.66, 125.83, 125.82, 123.95, 21.57.
#
6-Chloro-2-(3,4-dimethylphenyl)quinazoline (3cr)
Yellow solid; mp 142–143 °C; yield: 238.6 mg (89%).
1H NMR (400 MHz, CDCl3): δ = 9.30 (s, 1 H), 8.39–8.24 (m, 2 H), 7.96 (d, J = 8.9 Hz, 1 H), 7.87–7.73 (m, 2 H), 7.27 (d, J = 8.1 Hz, 1 H), 2.35 (d, J = 15.6 Hz, 6 H).
13C NMR (101 MHz, CDCl3): δ = 161.45, 159.39, 149.24, 139.96, 136.94, 135.18, 134.93, 132.40, 130.25, 130.10, 129.58, 126.18, 125.81, 123.83, 19.95, 19.92.
#
6-Chloro-2-(3,5-dimethylphenyl)quinazoline (3cs)
Yellow solid; mp 140–141 °C; yield: 241.3 mg (90%).
1H NMR (400 MHz, CDCl3): δ = 9.37 (s, 1 H), 8.20 (s, 2 H), 8.02 (d, J = 8.9 Hz, 1 H), 7.88 (s, 1 H), 7.81 (d, J = 8.9 Hz, 1 H), 7.16 (s, 1 H), 2.44 (s, 6 H).
13C NMR (101 MHz, CDCl3): δ = 161.60, 159.45, 149.26, 138.33, 137.46, 135.09, 132.70, 132.68, 130.33, 126.38, 125.85, 123.94, 21.44.
#
#
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/a-1755-4700.
- Supporting Information
-
References
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Corresponding Authors
Publication History
Received: 31 December 2021
Accepted after revision: 31 January 2022
Accepted Manuscript online:
31 January 2022
Article published online:
22 March 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
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- 2 Akduman B, Crawford ED. Urology 2001; 58: 49
- 3a Geyer CE, Forster J, Lindquist D, Chan S, Romieu CG, Pienkowski T, Jagiello-Gruszfeld A, Crown J, Chan A, Kaufman B, Skarlos D, Campone M, Davidson N, Berger M, Oliva C, Rubin SD, Stein S, Cameron D. N. Engl. J. Med. 2006; 355: 2733
- 3b Johnston S, Pippen JJr, Pivot X, Lichinitser M, Sadeghi S, Dieras V, Gomez HL, Romieu G, Manikhas A, Kennedy MJ, Press MF, Maltzman J, Florance A, O’Rourke L, Oliva C, Stein S, Pegram M. J. Clin. Oncol. 2009; 27: 5538
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- 7b Panja SK, Saha S. RSC Adv. 2013; 3: 14495
- 7c Panja SK, Dwivedi N, Saha S. Tetrahedron Lett. 2012; 53: 6167
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- 15b Irrgang T, Kempe R. Chem. Rev. 2019; 119: 2524
- 15c Zell T, Milstein D. Acc. Chem. Res. 2015; 48: 1979
- 16 Mondal A, Sahoo MK, Subaramanian M, Balaraman E. J. Org. Chem. 2020; 85: 7181
- 17 Das K, Mondal A, Pal D, Srimani D. Org. Lett. 2019; 21: 3223
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