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Open AccessArticle

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

1
Department of Organic Chemistry, Faculty of Chemistry, Voronezh State University, 1 Universitetskaya sq., Voronezh 394018, Russia
2
Department of Organic Chemistry, Faculty of Physics and Mathematics and Natural Sciences, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(11), 2035; https://doi.org/10.3390/molecules22112035
Received: 4 November 2017 / Revised: 16 November 2017 / Accepted: 20 November 2017 / Published: 22 November 2017
(This article belongs to the Collection Heterocyclic Compounds)
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. View Full-Text
Keywords: pyrrole; pyrrolo[3,4-b]pyrrole; bromomaleimide; aminocrotonate; domino reaction pyrrole; pyrrolo[3,4-b]pyrrole; bromomaleimide; aminocrotonate; domino reaction
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MDPI and ACS Style

Shikhaliev, K.; Sabynin, A.; Sekirin, V.; Krysin, M.; Zubkov, F.; Yankina, K. 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. Molecules 2017, 22, 2035.

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