93946-02-2Relevant academic research and scientific papers
Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds
Wang, Xiaoxia,Li, Zhifang,Zhu, Xiangming,Mao, Hui,Zou, Xuefei,Kong, Lichun,Li, Xinsheng
, p. 6510 - 6521 (2008/09/21)
Promoted by triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between N-crotonoylbenzotriazole and aliphatic amines. However, normal 1,4-addition could occur between α,β-unsaturated aliphatic N-acylbenzotriazoles and aromatic amines, leading to β-amino N-acylbenzotriazoles 4 in good yields. In addition, exclusive 1,2-addition of aliphatic amines to N-cinnamoylbenzotriazoles gave excellent yields of cinnamides 5. Accordingly, three possible routes were proposed to rationalize the formation of compounds 3-5. Finally, with o-phenylenediamine and o-aminothiophenol as the substrates, the 1,4- and 1,2-addition to α,β-unsaturated N-acylbenzotriazoles could take place concurrently and the corresponding heterocycles 1,5-benzodiazepine-2-one and 1,5-benzothiazepine-4-one were constructed, respectively.
Efficient syntheses of β-amino-N-acylbenzotriazoles and cinnamides through regioselective 1,4- or 1,2-addition of amines to N- cinnamoylbenzotriazoles
Wang, Xiaoxia,Zou, Xuefei,Li, Jian,Hu, Qinghong
, p. 3042 - 3046 (2007/10/03)
Amines react with N-cinnamoylbenzotriazoles to afford either β-amino-N-acylbenzotriazoles or cinnamides depending on the structure of the amines. Aromatic amines react with N-cinnamoylbenzotriazoles via 1,4-addition to give β-amino-N-acyl-benzotriazoles in good yields. For o-phenylenediamine, the 1,4-addition products were further acylated to provide a facile route to substituted 1,3,4,5-tetrahydro-1,5-benzodiazepine-2-ones. Aliphatic amines, however, react exclusively through the 1,2-addition pathway to produce cinnamides in good yields. Georg Thieme Verlag Stuttgart.
