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

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.

Keywords:

• Dispiro pyrrolidines
• Azomethine ylide

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.