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A highly regioselective synthesis of 1-n-methyl-spiro-[2,3′“]-oxindole-spiro-[3,2”]indane-1“, 3”-dione-4-arylpyrrolidines through 1,3-dipolar cycloaddition protocol

✍ Scribed by A. R. Suresh Babu; R. Raghunathan; G. Gayatri; G. Narahari Sastry

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 451 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430609

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✦ Synopsis

Abstract

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2‐Arylidene‐1,3‐indanediones undergo a regioselective 1,3‐dipolar cycloaddition reaction with the azomethine ylide derived from isatin and sarcosine by decarboxylative route affording a series of 1‐N‐methyl — spiro[2.3′“]oxindole‐spiro[3.2”]indane‐1“,3”‐diones‐4‐aryl pyrrolidines. The structures were established by spectroscopic techniques as well as single crystal X‐ray analysis. Density functional theory at B3L YP/6‐31G^*^ and the semi empirical AM~1~ calculations were employed to rationalize the observed results. The experimental regioselectivity of 1,3‐dipolar cycloadditions could be corroborated nicely with the computed Fukui frontier orbital energies and reaction energies.

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