Pyrrole chemistry. XXIII. The cyanation of substituted pyrroles with chlorosulfonyl isocyanate (CSI). New syntheses of pyrrole-3-carbonitriles

1 September 1981

journal article
Published by Canadian Science Publishing in Canadian Journal of Chemistry

Vol. 59 (17) , 2673-2683
https://doi.org/10.1139/v81-384

Abstract

Chlorosulfonyl isocyanate (CSI) reacts not only with pyrrole itself but with pyrroles having powerful electron-withdrawing groups in the 2-position. Suitable choice of electron-withdrawing groups allows selective 4-substitution of the pyrrole ring. The N-chlorosulfonyl amides formed are readily converted to the corresponding nitriles. The procedure has been used to provide syntheses of pyrrole-3-carbonitrile and its 1-methyl homologue.

Keywords

SUBSTITUTION
CSI
ISOCYANATE
CORRESPONDING
CONVERTED
REACTS
CHLOROSULFONYL
SYNTHESES OF PYRROLE

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