Furan Ring Opening-Pyrrole
Ring Closure: A New Route to Pyrrolo[1,2-d][1,4]benzodiazepin-6-ones

Tatyana A. Nevolina; Vitaly A. Shcherbinin; Olga V. Serdyuk; Alexander V. Butin

doi:10.1055/s-0030-1260204

PAPER

Furan Ring Opening-Pyrrole Ring Closure: A New Route to Pyrrolo[1,2-d][1,4]benzodiazepin-6-ones

Tatyana A. Nevolina^a, Vitaly A. Shcherbinin^a, Olga V. Serdyuk^b, Alexander V. Butin*^a
^a Research Institute of Heterocyclic Compounds Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
Fax: +7(861)2596592; e-Mail: alexander_butin@mail.ru; e-Mail: av_butin@yahoo.com;
^b Department of Chemistry, Southern Federal University, Zorge 7, Rostov-on-Don 344090, Russian Federation

Abstract

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Abstract

A new method for the synthesis of pyrrolo[1,2-d][1,4]benzodiazepines is described. The method is based on the acid-catalyzed recyclization of N-[2-(5-alkyl-2-furyl)phenyl]-2-aminoacetamides and permits the formation of both diazepine and pyrrole rings in one pot. The reaction proceeds via furan ring opening to give the diketone moiety followed by consecutive reactions of the free amino group with both carbonyl functions.

Key words

furans - ring opening - ring closure - fused-ring system - pyrrolo[1,2-d][1,4]benzodiazepines - Paal-Knorr reaction

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