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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 7
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Original Articles

A Novel Entry into a New Class of Spiro Heterocyclic Framework: A Facile Synthesis of Dispiro[oxindole-1,2,3,4-tetrahydro-naphthalen-1-one]pyrrolidines and Spiro[1,2,3,4-tetrahydro-naphthalen-1-one]pyrrolidines

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Pages 1131-1139 | Received 15 May 2002, Published online: 21 Aug 2006
 

Abstract

2-Arylidene-1,2,3,4-tetrahydro-naphthalen-1-ones undergo regioselective 1,3-dipolar cycloaddition reaction with the azomethine ylide derived from isatin and sarcosine by decarboxylative route affording a series of 1-N-methyl-spiro[2.31]oxindole-spiro[3.211]111, 211,311,411, -tetrahydro-naphthalen-111-one-4-aryl-pyrrolidines. 2-Arylidene-1,2,3,4-tetrahydro-naphthalen-1-ones also undergo cycloaddition reaction with azomethine ylide derived from paraformaldehyde and sarcosine affording a series of 1-N-methyl-spiro[3.21]11,21,31,41-tetrahydro-naphthalen-11-one-4-aryl-pyrrolidines. The structures of the compounds were established by spectroscopic techniques.

Acknowledgments

AAR thanks Council of Scientific and Industrial Research (CSIR), New Delhi for the award of Senior Research Fellowship. Financial support from CSIR and UGC, New Delhi is gratefully acknowledged.

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