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

Abstract

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.

Metadata

Authors/Creators:	Choi, A. Coldham, I. https://orcid.org/0000-0003-4602-6292
Copyright, Publisher and Additional Information:	© 2019 Elsevier. This is an author produced version of a paper subsequently published in Tetrahedron Letters. Uploaded in accordance with the publisher's self-archiving policy. Article available under the terms of the CC-BY-NC-ND licence (https://creativecommons.org/licenses/by-nc-nd/4.0/).
Keywords:	Azomethine ylide; 1,3-Dipolar cycloaddition; Heterocycle; Multicomponent reaction
Dates:	Accepted: 7 August 2019 Published (online): 8 August 2019 Published: 12 September 2019
Institution:	The University of Sheffield
Academic Units:	The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield)
Depositing User:	Symplectic Sheffield
Date Deposited:	16 Dec 2019 15:49
Last Modified:	08 Aug 2020 00:38
Status:	Published
Publisher:	Elsevier
Refereed:	Yes
Identification Number:	https://doi.org/10.1016/j.tetlet.2019.151023
Related URLs:	Author

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

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