1-Cyano-3-(1H)-1,2-benziodoxols: stable cyanoiodinanes and efficient reagents for direct N-alkyl cyanation of N,N-dialkylarylamines

Viktor Zhdankin, Chris J. Kuehl, Alexei P. Krasutsky, Jason T. Bolz, Brian Mismash, Jessica K. Woodward, Angela J. Simonsen

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Abstract

Cyanobenziodoxols 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystalline compounds. Cyanobenziodoxol 2 reacts with N,N-dimethylary lamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.

Original languageEnglish (US)
Pages (from-to)7975-7978
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number44
DOIs
StatePublished - Oct 30 1995

Bibliographical note

Funding Information:
Acknowledgement. This work was supported by a Cottrell College Science Award of Research Corporation; a research grant from the National Science Foundation (NSFXHE-9505868); a grant from the Donors of The Petroleum Research Fund, administered by the ACS; the University of Minnesota Graduate School Grant-in-Aid; the UMD Department of Chemistry Summer 1995 Undergraduate Research Program, and a Fellowship Award for A.J.S. from the CURSOR program.

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