A new synthetic method is developed which enables a direct one-step introduction of a cyano group into electron-rich heterocyclic systems of the indole, pyrrole, and indolizine series, and also to enamines using isocyanatophosphoryl dichloride.

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I s o c y a n a t o p h o s p h o r y l D i c h l o r i d e f o r C a r b a m o y l G r o u p I n t r o d u c t i oAbstract: A study on the stepwise hydrolysis of hetarene-and cycloalkenecarboxamidophosphoryl dichlorides afforded the synthesis of hitherto unknown hetarene-and cycloalkenecarboxamidophosphoric acids as well as allowing the introduction of unsubstituted carbamoyl group in the molecules of pyrroles, indoles, indolizines, and some enamines.

Phosphorylation of N-trimethylsilyland N-dimethyl-tert-butylsilylpyrroles with phosphorus tribromide in pyridine proceeds selectively at position 3 of the pyrrole ring. Removal of the trialkylsilyl protecting group has furnished the first representatives of N-unsubstituted 3-phosphorylated pyrroles.

The phosphorylation of N‐methylpyrrole with phosphorus (III) halides has been studied. Migration of the dibromophosphino group from the second to the third position of N‐methylpyrrole, leading to the 3‐dibromophosphine, has been found. Methods for the synthesis of 2,4‐bisphosphorylated pyrroles have been developed. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10:213–221, 1999

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