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Synthesis 2011(21): 3547-3551  
DOI: 10.1055/s-0030-1260204
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Tatyana A. Nevolinaa, Vitaly A. Shcherbinina, Olga V. Serdyukb, 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
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Publication History

Received 18 July 2011
Publication Date:
02 September 2011 (online)

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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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