Tetrahedron

The introduction of nitrile-groups into heterocycles and conversion of carboxylic groups into their corresponding nitriles with chlorosulfonylisocyanate and …

H Vorbrüggen, K Krolikiewicz

Index: Vorbrueggen, Helmut; Krolikiewicz, Konrad Tetrahedron, 1994 , vol. 50, # 22 p. 6549 - 6558

Full Text: HTML

Citation Number: 54

Abstract

Addition of chlorosulfonylisocyanate (CSI) to heterocycles such as thiophene (4) or indole (15) and unsaturated systems such as dihydropyran (7) gives N-chlorosulfonylamides RCONHSO2Cl, which can be converted by equivalent amounts of triethylamine to their corresponding nitriles. Since carboxylic acids react with CSI to N-chlorosulfonylamides, subsequent treatment with triethylamine affords the corresponding nitriles, but no ...