An efficient aldol-type direct reaction of isatins with TMSCH2CN

V. U. Bhaskara Rao; Krishna Kumar; Ravi P. Singh

doi:10.1039/C5OB01560J

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An efficient aldol-type direct reaction of isatins with TMSCH₂CN†

V. U. Bhaskara Rao,^a Krishna Kumar^a and Ravi P. Singh*^a

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^a Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi, India 110016
E-mail: ravips@chemistry.iitd.ac.in

Abstract

Cesium fluoride catalyzed direct cyanomethylation of various isatins by using trimethylsilyl acetonitrile (TMSAN) as a nucleophile has been developed. The reaction has been explored for a number of isatins, with various substitutions on its aromatic ring. Further, the versatility of the reaction is demonstrated by converting the direct aldol adducts to the corresponding intermediates of natural products and medicinally important compounds.

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Article information

DOI: https://doi.org/10.1039/C5OB01560J
Article type: Communication
Submitted: 28 Jul 2015
Accepted: 26 Aug 2015
First published: 26 Aug 2015

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Org. Biomol. Chem., 2015,13, 9755-9759

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An efficient aldol-type direct reaction of isatins with TMSCH₂CN

V. U. Bhaskara Rao, K. Kumar and R. P. Singh, Org. Biomol. Chem., 2015, 13, 9755 DOI: 10.1039/C5OB01560J

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Organic & Biomolecular Chemistry