UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes To Give 2-Aminobenzamides
Dishu Zeng
a
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
,
Tianbao Yang
a
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
,
Niu Tang
a
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
,
Wei Deng∗
a
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
,
Jiannan Xiang
a
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
,
Shuang-Feng Yin
a
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
,
Nobuaki Kambe
b
The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibarakishi, Osaka 567-0047, Japan
a
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
› InstitutsangabenNational Natural Science Foundation of China (21676076, 21878071, 21971060), Recruitment Program for Foreign Experts of China (WQ20164300353), Huxiang High-Talent Project of Hunan Province (2018RS3042).
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.
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.
Primary data for this article are available online at https://zenodo.org/record/5760133 and can be cited using the following DOI: 10.5281/zenodo.5760133.
