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Synfacts 2014; 10(3): 0301
DOI: 10.1055/s-0033-1340749
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Acridine Derivatives by ZnCl2-Promoted Intramolecular Cyclization

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Su Q, Li P, He M, Wu Q, * Ye L, Mu Y. * Jilin University, Changchun, P. R. of China
Facile Synthesis of Acridine Derivatives by ZnCl2-Promoted Intramolecular Cyclization of o-Arylaminophenyl Schiff Bases.

Org. Lett. 2014;
16: 18-21
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Publication History

Publication Date:
17 February 2014 (online)

 
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Key words

zinc - Schiff bases - acridines - intramolecular cyclization

Significance

The authors report a facile synthesis of acridines and dibenzophenanthrolines by the zinc(II) chloride promoted cyclization of o-arylaminophenyl Schiff bases, which are prepared from readily available 2-fluoro benzaldehyde. The corresponding polycyclic aza-arenes are obtained in excellent yields and, in most cases, with high ­regioselectivity.


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Comment

By double intramolecular cyclization reactions of bis(o-arylaminophenyl Schiff base) derivatives, complex dibenzophenanthrolines and acridinoacridine compounds are obtained. Noteworthy, an intramolecular cyclization does not occur if the imine nitrogen bears very sterically demanding substituents such as 2,6-i-Pr2C6H3.


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