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Synthesis 2011(15): 2495-2504  
DOI: 10.1055/s-0030-1260111
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Easy Access to Novel Sugar-Based Spirooxindole-pyrrolidines or -pyrrolizidines through [3+2] Cycloaddition of Azomethine Ylides

Arasappan Hemamalinia, Subbiah Nagarajana, Pawar Ravinderb, Venkatesan Subramanianb, Thangamuthu Mohan Das*a
a Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai - 600 025, India
Fax: +91(44)22352494; e-Mail: tmdas_72@yahoo.com;
b Chemical Laboratory, Central Leather Research Institute (CSIR), Adyar, Chennai, 600 020, India
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Publication History

Received 27 December 2010
Publication Date:
14 July 2011 (online)

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Abstract

An efficient one-pot synthesis of a library of novel sugar-based spirooxindole-pyrrolidines or -pyrrolizidines has been accomplished by [3+2] cycloaddition. This method utilizes an azo­methine ylide derived from isatin and sarcosine or l-proline with an α,β-unsaturated β-C-glycosidic ketone as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR (¹H and ¹³C), HPLC, and elemental analysis

Key words

4,6-O-butylidene-d-glucopyranose - α,β-unsaturated β-C-glycosidic ketones - cycloaddition - azomethine ylide - monospiroheterocyclics