Preprint Article Version 1 This version not peer reviewed

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

Version 1 : Received: 4 November 2017 / Approved: 6 November 2017 / Online: 6 November 2017 (06:43:10 CET)

A peer-reviewed article of this Preprint also exists.

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. 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.

Journal reference: Molecules 2017, 22, 2035
DOI: 10.3390/molecules22112035

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.

Subject Areas

pyrrole; pyrrolo[3,4-b]pyrrole; bromomaleimide; aminocrotonate; domino reaction

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