Three-component couplings for the synthesis of pyrroloquinoxalinones by azomethine ylide 1,3-dipolar cycloaddition chemistry

TETRAHEDRON LETTERS

卷:60

Article

Choi, Anthony¹  Coldham, Iain¹ 

[1] Univ Sheffield, Dept Chem, Brook Hill, Sheffield S3 7HF, S Yorkshire, England

关键词: Azomethine ylide;    1,3-Dipolar cycloaddition;    Heterocycle;    Multicomponent reaction;   

DOI  :  10.1016/j.tetlet.2019.151023

来源: Elsevier

【 摘 要 】

1-Methyl-3,4-dihydroquinoxalin-2(1H)-one was heated with a range of aldehydes to generate intermediate azomethine ylides which underwent [3 + 2] cycloaddition reactions with N-methyl or N-phenylmaleimide to give substituted tetrahydropyrroloquinoxalinones. Only one (racemic) stereoisomer was formed in each case and the stereochemical outcome was verified by single crystal X-ray analysis. The products from this multicomponent reaction could be oxidised with DDQ to the pyrroloquinoxalinones. Crown Copyright (C) 2019 Published by Elsevier Ltd. All rights reserved.

【 授权许可】

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