Regioselective Synthesis of Novel Spirooxindolo and Spiroindano Nitro Pyrrolidines Through 3+2 Cycloaddition Reaction

Abstract

β‐Nitro styrene reacts with nonstabilized azomethine ylides generated from isatin/ninhydrin with sarcosine, resulting in the formation of a series of spiroxindolo nitro pyrrolidines, and spiroindano nitro pyrrolidines, respectively, in good yields. It was noted that in a one‐pot 3+2 cycloaddition reaction, the azomethine ylides generated from isatin and ninhydrin have reacted with the β‐nitro styrenes regiochemically in opposite ways.

Keywords:

• Azomethine ylide
• cycloaddition
• β‐nitro styrenes
• regioselective
• spiropyrrolidines

Acknowledgment

The authors thank the Department of Science and Technology, New Delhi, India, for the financial support. One of the author, P. C., acknowledges K. K. Balasubramanian for his help in recording NMR spectra for some of the compounds reported here.