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.
![]() |
PDF
org_let_24-14_2772-2777_2022.pdf - Published Version Restricted to Registered users only Download (2MB) | Request a copy |
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 |
Actions (login required)
![]() |
View Item |