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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 12
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Original Articles

Simple and Convenient Approach for Synthesis of Tetrahydroquinoline Derivatives and Studies on Aza-Cope Rearrangement

, , &
Pages 1809-1828 | Received 25 Jan 2010, Published online: 29 Apr 2011
 

Abstract

A simple and novel synthesis of 1,2,3,4-tetrahydroquinoline derivatives by polyphosphoric acid–assisted reaction of N-aryl allyl anilines prepared from anilines has been reported. The generality and scope of the approach has been demonstrated by extending it to the synthesis of 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline (lilolidine) and 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline (julolidine). Further, Lewis acid–mediated aza-Cope rearrangement of various N-aryl allyl anilines has been demonstrated.

ACKNOWLEDGMENT

The authors thank Glenmark Pharmaceuticals Limited for granting permission to carry out the research work.

Notes

a All reactions completed within 10–15 min under a nitrogen atmosphere.

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