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Phosphorylation of 1-alkylmidazoles and 1-alkylbenzimidazoles with phosphorus(III) halides in the presence of bases

✍ Scribed by Andrej A. Tolmachev; Aleksandr A. Yurchenko; Anatolij S. Merculov; Marina G. Semenova; Evgenij V. Zarudnitskii; Vladimir V. Ivanov; Aleksandr M. Pinchuk

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 269 KB
Volume: 10
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1999)10:7<585::aid-hc12>3.0.co;2-u

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✦ Synopsis

Phosphorylation of 1-alkyl substituted imidazoles and benzimidazoles with P(III) halides in pyridine was shown to proceed at the 3-N atom of the heteroaryl ring and was followed by triethylamine-induced migration of the phosphorus group to the 2-C atom. Preparative methods were developed for the synthesis of a range of 2-phosphorylated derivatives of the indicated imidazoles. The latter were found to undergo alkylation either at P(III) or 3-N centers, depending on the alkylating agent.

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