24438-88-8Relevant articles and documents
Efficient, simple preparation of 1,3-diamine derivatives through addition of acrylamides with secondary amines
Liu, Yi,Hua, Ruimao,Qiu, Xianqing
, p. 1375 - 1380 (2005)
Reaction of acrylamides with secondary amines results in the formation of β-amino-propionamide through the addition reaction of N-H bond of amines across the double bond of acrylamides in the good to excellent yield. The structure of 2-methyl-3-(1-piperidinyl)-propionamide has been determined by X-ray analysis. Copyright Taylor & Francis, Inc.
Understanding water mediated proton migration in conversion of π-bond in olefinic carbon atoms into C–N bond to form β-amino adducts
Rathod, Prakash B.,Kumar, K.S. Ajish,Athawale, Anjali A.,Gopakumar, Gopinadhanpillai,Rao, C.V.S. Brahmmananda,Pandey, Ashok K.
, (2021/10/14)
The aza-Michael reactions with a variety of substrates were conducted in water affording the quantitative yields without any external catalyst, which is contrary to that published in literature. A more rational approach to analyze this problem was by conducting this conspicuous reaction with a variety of substrates in water and the results were analyzed using advanced theoretical calculations. Our investigation on the role of water in the reaction proposed a mechanism wherein water plays dual role both as medium as well as catalyst to facilitate the C–N bond formation using powerful tool in its armory, the “H-bonding”. Reactions were conducted in the absence of an external catalyst or co-solvents and, hence, are a greener approach in organic synthesis. The reactions of 15 examples were conducted with a variety of substrates to afford the addition products in the range of 70–95% yield. Theoretical studies on the transition state analysis suggested that it was the assistance of water, through H-bonding, that facilitated the conjugate addition of amine and proton transfer from ammonium ion, which could happen through two equally possible pathways.
Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
Majumdar, Biju,Mandani, Sonam,Bhattacharya, Tamalika,Sarma, Daisy,Sarma, Tridib K.
, p. 2097 - 2106 (2017/02/26)
Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.
DABCO-based ionic liquids: Recyclable catalysts for aza-michael addition of α,β-unsaturated amides under solvent-free conditions
Ying, Anguo,Li, Zhifeng,Yang, Jianguo,Liu, Shuo,Xu, Songlin,Yan, Hua,Wu, Chenglin
, p. 6510 - 6516 (2014/08/05)
An array of novel 1,4-diazobicyclo[2.2.2]octane (DABCO) based ionic liquids were developed and used as recyclable catalysts for the aza-Michael addition at room temperature without any organic solvent. [DABCO-PDO][OAc] was found to be the most efficient catalyst, and the amount of catalyst was only 10 mol %. Various amines reacted with a wide range of α,β-unsaturated amides, smoothly affording target products in good to excellent yields within hours. Moreover, the catalyst could be reused up to eight times, still maintaining a high catalytic activity. Finally, a plausible mechanism was proposed. FTIR and computational chemistry were used to verify the catalytic mechanism.
