A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis

Ghosh, A and Shee, S and Biju, AT (2022) A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis. In: Organic Letters, 24 (14). pp. 2772-2777.

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Abstract

N-Heterocyclic carbene-catalyzed formal 4+2 benzannulation of enals with suitably substituted pyrimidine-2,4-diones allowing the mild and facile synthesis of functionalized quinazoline-2,4-diones is presented. This oxidative transformation proceeds via the simultaneous generation of dienolates and α,β-unsaturated acylazoliums and follows a vinylogous Michael/aldol/β-lactonization/decarboxylation/oxidation sequence to afford quinazoline-2,4-diones, including axially chiral ones with suitable substitutions, in an operationally simple procedure. In addition, substituted coumarins as dienolate precursors afforded benzochromen-6-one derivatives. © 2022 American Chemical Society.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to American Chemical Society
Keywords:	article; catalysis; chirality; decarboxylation; lactonization; oxidation; synthesis
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	19 May 2022 05:46
Last Modified:	19 May 2022 05:46
URI:	https://eprints.iisc.ac.in/id/eprint/72018

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