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

Author: Prasada Rao Lingam V. S.   Thomas Abraham   Mukkanti Khagga   Gopalan Balasubramanian  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.41, Iss.12, 2011-01, pp. : 1809-1828

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Abstract

[image omitted] 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.