UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes To Give 2-Aminobenzamides

Dishu Zeng; Tianbao Yang; Niu Tang; Wei Deng; Jiannan Xiang; Shuang-Feng Yin; Nobuaki Kambe; Renhua Qiu

doi:10.1055/a-1736-4388

Synthesis, Table of Contents

Synthesis 2022; 54(10): 2361-2372
DOI: 10.1055/a-1736-4388

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UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes To Give 2-Aminobenzamides

Dishu Zeng

^aState 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

^aState 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

^aState 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∗

^aState 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

^aState 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

^aState 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

^bThe Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibarakishi, Osaka 567-0047, Japan

,

Renhua Qiu ∗

^aState 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

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Abstract

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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 - quinazolinone

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References

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