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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 15
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Original Articles

Synthesis of Spirooxindolo/Spiroindano Nitro Pyrrolizidines through Regioselective Azomethine Ylide Cycloaddition Reaction

Mahalingam Poornachandran Department of Organic Chemistry, University of Madras, Chennai, India
&
Ragavachary Raghunathan Department of Organic Chemistry, University of Madras, Chennai, IndiaCorrespondence[email protected]
Pages 2507-2517 | Received 12 Dec 2006, Published online: 09 Aug 2007
 
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Abstract

Synthesis of a series of spirooxindolonitro pyrrolizidines and spiroindanonitro pyrrolizidines has been accomplished. The nonstabilized azomethine ylides generated from isatin and ninhydrin with proline reacted with nitro styrenes to regioselectively yield spirocycloadducts.

Acknowledgments

Poornachandran thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for the award of a senior research fellowship (SRF). Financial support from the Department of Science and Technology (DST), New Delhi Fist Facility and DST‐FIST, Department of Science and Technology, New Delhi, India, is also gratefully acknowledged.

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