Canadian Journal of Chemistry

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

CE Loader, HJ Anderson

Index: Loader, Charles E.; Anderson, Hugh J. Canadian Journal of Chemistry, 1981 , vol. 59, p. 2673 - 2676

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Citation Number: 65

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.