Ghosh, Arghya ; Shee, Sayan ; Biju, Akkattu T. (2022) A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis Organic Letters, 24 (14). pp. 2772-2777. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.2c00954
Related URL: http://dx.doi.org/10.1021/acs.orglett.2c00954
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128579 |
| Deposited On: | 03 Nov 2022 06:38 |
| Last Modified: | 03 Nov 2022 06:38 |
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