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DOI: 10.1055/a-1736-4388
UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes To Give 2-Aminobenzamides
National Natural Science Foundation of China (21676076, 21878071, 21971060), Recruitment Program for Foreign Experts of China (WQ20164300353), Huxiang High-Talent Project of Hunan Province (2018RS3042).
Abstract
A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.
Key words
UV-light-induced - amidation - nitro reduction - 2-aminobenzamide - 2-aminobenzaldehyde - quinazolinoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1736-4388. Included are X-ray data of 4a (CCDC 2125130) and copies of the NMR spectra of 4a–p, 5a–k, 6a–e, 8 and 9.
- Supporting Information
Publication History
Received: 06 December 2021
Accepted after revision: 11 January 2022
Accepted Manuscript online:
11 January 2022
Article published online:
01 March 2022
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