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Synthesis 2011(21): 3547-3551
DOI: 10.1055/s-0030-1260204
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
Further Information
Received
18 July 2011
Publication Date:
02 September 2011 (online)
Publication History
Publication Date:
02 September 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201121/lookinside/thumbnails/10.1055-s-0030-1260204-1.jpg)
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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