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Synthesis 2018; 50(24): 4897-4904
DOI: 10.1055/s-0037-1610647
paper
© Georg Thieme Verlag Stuttgart · New York

Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones

Ekaterina E. Stepanova  *
Department of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian Federation   Email: caterina.stepanova@psu.ru   Email: koh2@psu.ru
,
Svetlana O. Kasatkina
,
Maksim V. Dmitriev
,
Andrey N. Maslivets*
Department of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian Federation   Email: caterina.stepanova@psu.ru   Email: koh2@psu.ru
› Author AffiliationsThis work was supported by the Russian Science Foundation, project # 17-73-10210.
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Publication History

Received: 27 April 2018

Accepted after revision: 04 July 2018

Publication Date:
20 August 2018 (online)

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Abstract

A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intramolecular cyclization reaction are predominantly formed under catalyst-free and solvent-free conditions. The proposed strategy provides facile access to pharmaceutically interesting pyrrole-based polyheterocycles.

Key words

aldol reaction - fused-ring systems - Michael addition - nitrogen heterocycles - polycycles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610647.
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