The introduction of nitrile-groups into heterocycles and conversion of carboxylic groups into their corresponding nitriles with chlorosulfonylisocyanate and triethylamine
1994; Elsevier BV; Volume: 50; Issue: 22 Linguagem: Inglês
10.1016/s0040-4020(01)89685-x
ISSN1464-5416
AutoresHelmut Vorbrüggen, Konrad Krolikiewicz,
Tópico(s)Synthesis and Biological Evaluation
ResumoAddition 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 isocyanates as claimed by other authors. The mechanisms of the conversion of the intermediate N-chlorosulfonylamides into the corresponding nitriles are discussed.
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