23784-65-8Relevant academic research and scientific papers
Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 788 - 792 (2020/05/19)
A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid
Ghosh, Santanu,Jana, Chandan K.
supporting information, p. 5803 - 5807 (2019/11/11)
A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation of undesired chemical wastes that generally originate from the use of coupling reagents, oxidants, or catalysts has been avoided to make this reaction more atom economical.
SmI3-catalyzed addition of amines to α,β-unsaturated N-acylbenzotriazoles
Wang, Xiaoxia,He, Liang,Li, Zhifang,Wang, Wencun,Liu, Junhua
experimental part, p. 819 - 829 (2009/08/08)
The addition of amines to α,β-unsaturated N-acylbenzotriazoles could be catalyzed by samarium triiodide (SmI3) at ambient temperature. α,β-Unsaturated aliphatic N-acylbenzotriazoles afforded bis-addition products (β-amino amides), whereas N-cinnamoylbenzo
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.
