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Synfacts 2014; 10(3): 0308
DOI: 10.1055/s-0033-1340751
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Azomethine Imines by Intramolecular Cycloaddition Reaction

Contributor(s):
Paul Knochel
,
Thomas Klatt
Bercovici DA, Ogilvie JM, Tsvetkov N, Brewer M * University of Vermont, Burlington, USA
Intramolecular Polar [4++2] Cycloadditions of Aryl-1-aza-2-azoniaallene Salts: Unprecedented Reactivity Leading to Polycyclic Protonated Azomethine Imines.

Angew. Chem. Int. Ed. 2013;
52: 13338-13341
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Publication History

Publication Date:
17 February 2014 (online)

 
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Key words

cumulenes - cycloaddition - heterocycles - azomethine imines

Significance

Brewer and co-workers report an unprecedented reactivity of aryl-1-aza-2-azonia­allene salts: A cycloaddition reaction occurs at low temperature and provides high yields of protonated azomethine imine products which contain a 1,2,3,4-tetrahydrocinnoline core.


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Comment

The protocol is fairly general with respect to alkene substitution, and the products, containing all-carbon or nitrogen-bearing quaternary centers, are obtained in high yields.


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