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Synfacts 2008(11): 1155-1155  
DOI: 10.1055/s-0028-1083481
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Tetrahydroquinolines by an Imino-Diels-Alder Reaction

Contributor(s): Victor Snieckus, Dmitry N. Korolev
C. M. Dehnhardt*, Y. Espinal, A. M. Venkatesan
Wyeth Research, New York, USA
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

Reported is a synthesis of 1,2,3,4-tetrahydroquinolines by the Diels-Alder reaction of alkenes with iminium salts formed in situ from N-methylaniline and different sources of formaldehyde. The influence of the source of formaldehyde, Lewis acid and alkene structure on yield and stereochemistry of the products obtained was moderately investigated. The formation of both syn and anti products suggests the competition of pericyclic [4+2] cycloaddition with a stepwise mechanism involving cationic species.