Application of N,N‑Dimethylethanolamine as a One-Carbon Synthon for the Synthesis of Pyrrolo[1,2‑a]quinoxalines, Quinazolin-4-ones, and Benzo[4,5]imidazoquinazolines via [5 + 1] Annulation

The synthesis of N-heterocycles composes a significant part of synthetic chemistry. In this report, a Cu­(II)-catalyzed green and efficient synthesis of pyrrolo­[1,2-a]­quinoxaline, quinazolin-4-one, and benzo­[4,5]­imidazoquinazoline derivatives was developed, employing N,N-dimethylethanolamine (DM...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (21), p.14753-14762
Main Authors: Geng, Meiqi, Huang, Minzhao, Kuang, Jinqiang, Fang, Weiwei, Miao, MaoZhong, Ma, Yongmin
Format: Article
Language:English
Subjects:
Carbon
Deanol
Pyrroles
Quinoxalines
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Summary:The synthesis of N-heterocycles composes a significant part of synthetic chemistry. In this report, a Cu­(II)-catalyzed green and efficient synthesis of pyrrolo­[1,2-a]­quinoxaline, quinazolin-4-one, and benzo­[4,5]­imidazoquinazoline derivatives was developed, employing N,N-dimethylethanolamine (DMEA) as a C1 synthon. Green oxidant O2 is critical in these transformations, facilitating the formation of a key intermediatea reactive iminium ion. The method conducted under mild conditions is compatible with a diversity of functional groups, providing an appealing alternative to the previously developed protocols.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02079