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

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...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) no. 21; pp. 3547 - 3551
Main Authors Nevolina, Tatyana A., Shcherbinin, Vitaly A., Serdyuk, Olga V., Butin, Alexander V.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Paal-Knorr reaction
ring opening
pyrrolo[1,2-d][1,4]benzodiazepines
furans
ring closure
DIAZEPINES
fused-ring system
Online AccessGet more information

Cover

More Information
Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1260204