Herein we disclose an efficient and flexible approach to biologically relevant 3,4-dihydropyrazino[1,2-alpha] indol-1(2H)ones and 3,4-dihydropyrrolo[1,2-alpha]pyrazin-1(2H)ones through a domino Michael/intra-molecular nucleophilic substitution pathway using potassium hydroxide in dichloromethane. Variously substituted vinyl selenones and 1H-indole-2-carboxamides or 1H-pyrrole-2-carboxamides have been employed with success in chemo and regio-selective processes. The introduction of an amino acid portion on the amidic function is well tolerated without racemization. (C) 2018 Elsevier Ltd. All rights reserved.

A domino approach to pyrazino- indoles and pyrroles using vinyl selenones

Palomba M;Sancineto, L.;Marini, F.;Santi, C.;Bagnoli, L.
2018

Abstract

Herein we disclose an efficient and flexible approach to biologically relevant 3,4-dihydropyrazino[1,2-alpha] indol-1(2H)ones and 3,4-dihydropyrrolo[1,2-alpha]pyrazin-1(2H)ones through a domino Michael/intra-molecular nucleophilic substitution pathway using potassium hydroxide in dichloromethane. Variously substituted vinyl selenones and 1H-indole-2-carboxamides or 1H-pyrrole-2-carboxamides have been employed with success in chemo and regio-selective processes. The introduction of an amino acid portion on the amidic function is well tolerated without racemization. (C) 2018 Elsevier Ltd. All rights reserved.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/1444094
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