A new synthetic route to polyhydrogenated pyrrolo[3,4-b]pyrroles by the domino reaction of 3-bromopyrrole-2,5-diones with aminocrotonic acid esters

A new synthetic approach to polyfunctional hexahydropyrrolo[3,4-b]pyrroles was developed based on cyclization of N-arylbromomaleimides with aminocrotonic acid esters. A highly chemo- and stereoselective reaction is a Hantzsch-type domino process, involving the steps of initial nucleophilic C-addition or substitution and subsequent intramolecular nucleophilic addition without recyclyzation of imide cycle. © 2017 by the authors.

Authors
Shikhaliev K.1 , Sabynin A.1 , Sekirin V.1 , Krysin M.1 , Zubkov F. 2 , Yankina K. 2
Journal
Molecules
Publisher
MDPI AG
Number of issue
11
Language
English
Status
Published
Link
External link
DOI
10.3390/molecules22112035
Number
2035
Volume
22
Year
2017
Organizations
  • 1 Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, 1 Universitetskaya sq., Voronezh, 394018, Russian Federation
  • 2 Department of Organic Chemistry, Faculty of Physics and Mathematics and Natural Sciences, RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
Keywords
Aminocrotonate; Bromomaleimide; Domino reaction; Pyrrole; Pyrrolo[3,4-b]pyrrole
Date of creation
19.10.2018
Date of change
12.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/5214/
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