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Synthesis 2022; 54(14): 3298-3306
DOI: 10.1055/a-1792-9930
paper

Rhodium(III)-Catalyzed Synthesis of Quinazolin-4(3H)-ones with N-Methoxyamides as Synthesis Reagents

Guanyu Zhou
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Zhibin Huang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Xu Xu
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Zhang Fang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Pengcheng Huang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Zefeng Deng
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Bao Li∗
b   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453000, P. R. of China
,
Yingsheng Zhao∗
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
b   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453000, P. R. of China
› Author AffiliationsThis work was supported by Natural Science Foundation of China (Nos. 21772139, 22171197), the Major Basic Research Project of the Natural Science Foundation of Jiangsu Higher Education Institutions (21KJA150002), National local joint engineering laboratory to functional adsorption material technology for the environmental protection (SDGC2121) and the PAPD Project. The project was also supported by the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University.
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Abstract

A practical method to synthesize quinoxalinones via intra/intermolecular amination using rhodium as the catalyst was developed. A wide variety of quinoxalinones were prepared from N-methoxybenzamides in moderate to excellent yields. Gram-scale reactions were also achieved, highlighting the synthetic importance of this new transformation.

Key words

rhodium - quinazolin-4(3H)-one - C–H activation - cyclization - N-methoxyamide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1792-9930.
  • Supporting Information


Publication History

Received: 22 December 2021

Accepted after revision: 09 March 2022

Accepted Manuscript online:
09 March 2022

Article published online:
25 April 2022

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