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Molecules 2017, 22(11), 2035; doi:10.3390/molecules22112035

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.
Received: 4 November 2017 / Revised: 16 November 2017 / Accepted: 20 November 2017 / Published: 22 November 2017
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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