23784-74-9Relevant academic research and scientific papers
Microwave-assisted aminocarbonylation of ynamides by using catalytic [Fe3(CO)12] at low pressures of carbon monoxide
Pizzetti, Marianna,Russo, Adele,Petricci, Elena
supporting information; experimental part, p. 4523 - 4528 (2011/06/20)
The microwave-assisted aminocarbonylation of ynamides at low pressures of CO is reported. A new class of (E)-acrylamides that are potentially suitable for several applications has been regioselectively synthesized after microwave irradiation for only 20 min by using eco-friendly [Fe3(CO) 12] as the catalyst precursor and triethylamine as the ligand. This transformation is atom economic as all reactants are used in stoichiometric quantities. Furthermore, the transformation is efficiently applied to the alkoxycarbonylation of alkynes as well. Moreover, running these reactions under microwave irradiation allows the simplification of the reaction conditions with remarkable reductions in time, temperature and gas pressure.
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.
Stereoselective synthesis of 3,4-trans-disubstituted γ-lactams by cerium(IV) ammonium nitrate mediated radical cyclization of cinnamamides
Nair, Vijay,Mohanan, Kishor,Suja, Tachapully D.,Biju, Akkattu T.
, p. 1179 - 1184 (2008/02/04)
A facile synthesis of 3,4-trans-disubstituted γ-lactams was developed, consisting of the radical cyclization of cinnamamides mediated by cerium(IV) ammonium nitrate. The single-electron-transfer (SET) reaction of the methoxystyrenyl moiety mediated by cer
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.
