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DOI: 10.1055/s-0037-1610647
Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones
This work was supported by the Russian Science Foundation, project # 17-73-10210.Publikationsverlauf
Received: 27. April 2018
Accepted after revision: 04. Juli 2018
Publikationsdatum:
20. August 2018 (online)
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 - polycyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610647.
- Supporting Information