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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 Full article

Journal Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263
Output data Year: 2019, Volume: 84, Number: 21, Pages: 13707-13720 Pages count : 14 DOI: 10.1021/acs.joc.9b01925
Authors Zelina Elena Y. 1 , Nevolina Tatyana A. 1 , Skvortsov Dmitry A. 2,3 , Trushkov Igor V. 4,5 , Uchuskin Maxim G. 1
Affiliations
1 Perm State University, Bukireva st. 15, Perm 614990 Russian Federation
2 M.V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russian Federation
3 Higher School of Economics, Myasnitskaya st. 13, Moscow 101000, Russian Federation
4 D. Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela st. 1, Moscow 117997, Russian Federation
5 N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russian Federation

Abstract: 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.
Cite: Zelina E.Y. , Nevolina T.A. , Skvortsov D.A. , Trushkov I.V. , Uchuskin M.G.
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
Journal of Organic Chemistry. 2019. V.84. N21. P.13707-13720. DOI: 10.1021/acs.joc.9b01925 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000494562600045
Scopus: 2-s2.0-85074370265
OpenAlex: W2974281049
Citing:
DB Citing
OpenAlex 20
Scopus 20
Web of science 16
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