Synthesis of Novel Spiroheterocycles Through 1,3-Dipolar Cycloaddition of Azomethine Ylides with Triarylideneacetylacetone Through Decarboxylation

Abstract

Triarylideneacetylacetone undergoes regioselective 1,3-dipolar cycloaddition reactions with azomethine ylide derived from isatin and L-proline/sarcosine/octahydro-1H-indole-2-carboxylic acid by decarboxylation, affording a series of spiroheterocycles. This one-pot, three-component tandem reaction is efficient and yields novel spiroheterocylic compounds in good yields. The structure and stereochemistry of the cycloadduct have been established by single-crystal x-ray and spectroscopic techniques.

Keywords:

• Azomethine ylide
• 1,3-dipolar cycloaddition
• spiropyrrolidine
• spiropyrrolizine
• triarylideneacetylacetone

ACKNOWLEDGMENT

One of the authors, R. M., thanks Dr. Raghavendra Rao, managing director of Orchid Research Laboratories Limited, Chennai, India (www.orchidpharma.com), for consent to perform the research.