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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 3
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Original Articles

A High Regioselective Synthesis of Novel Dispiro[oxindole-cyclohexanone]pyrrolidines

Ambrose Amal Raj Department of Organic Chemistry, University of Madras, A. C. College Campus, Chennai, Tamil Nadu, India
&
Raghavachary Raghunathan Department of Organic Chemistry, University of Madras, A. C. College Campus, Chennai, Tamil Nadu, IndiaCorrespondence[email protected]
Pages 421-426 | Received 21 Jan 2002, Published online: 17 Aug 2006
 
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Abstract

A simple and efficient synthesis of title compounds has been accomplished by regioselective 1,3-dipolar cycloaddition reaction of azomethine ylide generated by the decarboxylative condensation of isatin and sarcosine with (E)-2-arylidene-1-cyclohexanones. The regio and stereochemistry of products were determined by spectroscopic techniques. The synthesis proceeds in good yield to afford a series of novel dispiro[oxindole-cyclohexanone]pyrrolidines, 1-N-methyl-spiro-[2.31]oxindole-spiro[3.211]111-cyclohexanone-4-aryl-pyrrolidines.

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.

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