1. An Intramolecular Schmidt Reaction of δ-Azido N-Acylbenzotriazoles
- Author
-
Jing Zhu, Chun-Fang Liu, Peiming Gu, Shao-Lei Ding, and Zhi-Qi Cao
- Subjects
chemistry.chemical_classification ,Benzotriazole ,010405 organic chemistry ,Chemistry ,viruses ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Isocyanate ,Medicinal chemistry ,0104 chemical sciences ,Ion ,chemistry.chemical_compound ,Nucleophile ,Intramolecular force ,Schmidt reaction ,Lewis acids and bases ,Physical and Theoretical Chemistry ,Alkyl - Abstract
A Lewis acid promoted intramolecular Schmidt reaction of N-acylbenzotriazoles with alkyl azides was designed and realized. The benzotriazole was not only employed as an efficient activator for initiating the Schmidt rearrangement but also used as a powerful terminator for the subsequent nucleophilic trapping of the isocyanate ion and/or N-acyliminium ion from the rearrangement. Thirteen δ-azido N-acylbenzotriazoles were investigated, and the conversion afforded the desired benzotriazole-1-carboxamides and lactams with good to excellent yields.
- Published
- 2021