A Route to (Het)arene-Annulated Pyrrolo[1,2‑d][1,4]diazepines via the Expanded Intramolecular Paal–Knorr Reaction: Nitro Group and Furan Ring as Equivalents of Amino Group and 1,4-Diketone

A straightforward protocol toward pharmacologically relevant (het)­areno­[x,y-b]­pyrrolo­[1,2-d]­[1,4]­diazepines in good to high yields has been described. The designed approach consists of an acid-promoted furan ring opening in easily accessible N-(2-furylethyl)-2-nitroanilines or their heterocycl...

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Published inJournal of organic chemistry Vol. 84; no. 21; pp. 13707 - 13720
Main Authors Zelina, Elena Y, Nevolina, Tatyana A, Skvortsov, Dmitry A, Trushkov, Igor V, Uchuskin, Maxim G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2019
Amer Chemical Soc
Subjects
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
furans
nitro compounds
Physical Sciences
Science & Technology
THERAPEUTIC EFFICACY
PHARMACOKINETIC PROPERTIES
BROMOPYRROLE ALKALOIDS
PYRROLIZINES
DERIVATIVES
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Summary:A straightforward protocol toward pharmacologically relevant (het)­areno­[x,y-b]­pyrrolo­[1,2-d]­[1,4]­diazepines in good to high yields has been described. The designed approach consists of an acid-promoted furan ring opening in easily accessible N-(2-furylethyl)-2-nitroanilines or their heterocyclic analogues followed by the reductive cyclization of the corresponding nitro-1,4-diketones.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.9b01925