volume 24 issue 14 pages 2772-2777

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

Publication typeJournal Article
Publication date2022-04-04
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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.
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GOST Copy
Ghosh A., Shee S., Biju A. A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis // Organic Letters. 2022. Vol. 24. No. 14. pp. 2772-2777.
GOST all authors (up to 50) Copy
Ghosh A., Shee S., Biju A. A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis // Organic Letters. 2022. Vol. 24. No. 14. pp. 2772-2777.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.2c00954
UR - https://doi.org/10.1021/acs.orglett.2c00954
TI - A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis
T2 - Organic Letters
AU - Ghosh, Arghya
AU - Shee, Sayan
AU - Biju, A.T
PY - 2022
DA - 2022/04/04
PB - American Chemical Society (ACS)
SP - 2772-2777
IS - 14
VL - 24
PMID - 35377662
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Ghosh,
author = {Arghya Ghosh and Sayan Shee and A.T Biju},
title = {A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.orglett.2c00954},
number = {14},
pages = {2772--2777},
doi = {10.1021/acs.orglett.2c00954}
}
MLA
Cite this
MLA Copy
Ghosh, Arghya, et al. “A Benzannulation Strategy for Rapid Access to Quinazoline-2,4-diones via Oxidative N-Heterocyclic Carbene Catalysis.” Organic Letters, vol. 24, no. 14, Apr. 2022, pp. 2772-2777. https://doi.org/10.1021/acs.orglett.2c00954.