Regioselective Synthesis of Dispirocycloalkanooxindolopyrrolidines and Dispirocyclalkanoindanopyrrolidines

Abstract

Synthesis of a series of novel dispirocycloalkanone-oxindolopyrrolidines and dispirocycloalkanone-indanopyrrolidines is described. The nonstabilized azomethine ylides generated from a secondary amino acid, sarcosine, and carbonyl components (isatin and ninhydrin) have been effectively trapped by the dipolarophiles, arylidene cycloalkanones, to afford dispiropyrrolidines. The one-pot azomethine ylide cycloaddition reactions were highly regioselective.

Keywords:

• Azomethine ylide
• dipolarophile
• oxindole
• regioselective
• spiropyrrolidine

ACKNOWLEDGMENTS

Poornachandran thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for the award of senior research fellowship (SRF). M. J. thanks the University Grants Commission (UGC) for the fellowship. Financial support from DST and DST-FIST (Department of Science and Technology), New Delhi, India, is also gratefully acknowledged.