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Issue 27, 2020
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Diverse reactivity of isatin-based N,N′-cyclic azomethine imine dipoles with arynes: synthesis of 1′-methyl-2′-oxospiro [indene-1,3′-indolines] and 3-aryl-3-pyrazol-2-oxindoles

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Abstract

The reaction of aryne with isatin-based N,N′-cyclic azomethine imine 1,3-dipole afforded 3,3-disubstituted oxindole bearing a pyrrolidine ring and a quaternary stereocenter in very good yield. In contrast, methyl substitution on the pyrrolidine ring of 1,3-dipole directed [3+2] cycloaddition with aryne gave a mixture of column separable diastereomers of the cycloadduct with moderate diastereoselectivity in excellent yield. A plausible reaction mechanism is provided. The experimental results were supported by DFT calculations. Furthermore, the synthesized 3,3-disubstituted oxindole was synthetically transformed to a 1,3-diyne derivative.

Graphical abstract: Diverse reactivity of isatin-based N,N′-cyclic azomethine imine dipoles with arynes: synthesis of 1′-methyl-2′-oxospiro [indene-1,3′-indolines] and 3-aryl-3-pyrazol-2-oxindoles

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Article information


Submitted
04 Apr 2020
Accepted
09 Jun 2020
First published
10 Jun 2020

New J. Chem., 2020,44, 11593-11601
Article type
Paper

Diverse reactivity of isatin-based N,N′-cyclic azomethine imine dipoles with arynes: synthesis of 1′-methyl-2′-oxospiro [indene-1,3′-indolines] and 3-aryl-3-pyrazol-2-oxindoles

R. S. Meerakrishna, S. S. Smile, M. Athira, V. S. K. Choutipalli and P. Shanmugam, New J. Chem., 2020, 44, 11593
DOI: 10.1039/D0NJ01684E

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