16490-80-5Relevant academic research and scientific papers
Significant rate acceleration of the aza-Michael reaction in water
Ranu, Brindaban C.,Banerjee, Subhash
, p. 141 - 143 (2007)
The addition of amines to conjugated alkenes has been carried out in water at room temperature very efficiently without any catalyst. Significant rate acceleration of this reaction is observed in water compared to organic solvents.
Boric acid: A novel and safe catalyst for aza-Michael reactions in water
Chaudhuri, Mihir K.,Hussain, Sahid,Kantam, M. Lakshmi,Neelima
, p. 8329 - 8331 (2005)
Boric acid efficiently catalyzes the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds, with great alacrity and excellent yields, in water under mild conditions. Aromatic amines do not participate effectively in the reaction.
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.
Synthesis and biological evaluation of 4-hydroxy-5-oxo-2,5-dihydro-1: H -pyrrole-3-carboxamides and their zinc(II) complexes as candidate antidiabetic agents
Saito, Ryota,Tamura, Moe,Kawano, Saya,Yoshikawa, Yutaka,Kato, Akihiro,Sasaki, Kaname,Yasui, Hiroyuki
supporting information, p. 5572 - 5581 (2017/07/10)
The newly designed 1-(arylmethyl)-2,5-dihydro-4-hydroxy-5-oxo-1H-pyrrole-3-carboxamides (1a-e) were synthesized by using N-tritylated acrylamide as a starting material, and their zinc(ii) complexes (10a-e) were readily prepared by simply mixing 1a-e and ZnSO4 in the presence of LiOH. The aldose reductase (AR) inhibitory activity of 1a-e was evaluated to reveal important structural features for 2,5-dihydro-5-oxo-1H-pyrrole derivatives to exhibit high AR inhibitory activity. The in vitro insulin-mimetic activity of these complexes was evaluated from 50% inhibitory concentrations (IC50) on free fatty acid (FFA) release from isolated rat adipocytes treated with epinephrine. Four out of the five newly synthesized complexes exhibited higher in vitro insulin-mimetic activities than ZnSO4, a positive control. This study proved that the newly synthesized N2O2-coordination-type zinc(ii) complexes based on pyrrole-3-carboxamide derivatives (1a-d) are potential hypoglycemic agents.
Ionic liquid catalyzed amines with unsaturated amide aza-Michael addition method
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Paragraph 0028; 0029, (2016/11/24)
The invention relates to an ionic liquid catalyzed amine and unsaturated amide aza-Michael addition method which is realized under the reaction conditions of an efficient and environment-friendly catalyst, no solvent and room temperature. The method comprises the step of with an ionic liquid as a catalyst, enabling amines and unsaturated amides to be subjected to aza-Michael addition reaction at room temperature and normal pressure to obtain a corresponding addition product, wherein the ionic liquid is repeatedly used eight times, and the catalytic reaction yield is not remarkably reduced. The method is simple in operation, high in yield, good in reusability of a catalytic reaction system, mild in reaction condition and wide in industrial application prospect.
[CH3COO]: Efficient and recyclable catalyst for aza-Michael addition of α, β-unsaturated compounds and amines under solvent-free conditions
Gao, Xiaochong,Gao, Ruichang
, p. 9101 - 9112 (2015/03/04)
The recyclable ionic liquid [ADPQ][CH3COO] has been used as catalyst for aza-Michael addition of amines to α, β-unsaturated compounds to produce β-amino compounds. The reactions were complete in a few hours with high yields. The ionic liquid can be recycled and reused six times without noticeable decrease of catalytic activity.
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.
Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes
Verma, Sanny,Mungse, Harshal P.,Kumar, Neeraj,Choudhary, Shivani,Jain, Suman L.,Sain, Bir,Khatri, Om P.
supporting information; experimental part, p. 12673 - 12675 (2012/01/05)
Graphene oxide was found to be a highly efficient, reusable and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes to furnish corresponding β-amino compounds in excellent yields. The Royal Society of Chemistry 2011.
An efficient biomaterial supported bifunctional organocatalyst (ES-SO 3- C5H5NH+) for the synthesis of β-amino carbonyls
Verma, Sanny,Jain, Suman L.,Sain, Bir
experimental part, p. 2314 - 2318 (2011/05/02)
A biomaterial supported organocatalyst, readily synthesized by the reaction of chemically modified sulfonic group containing expanded corn starch with pyridine exhibited excellent catalytic activity for the synthesis of β-amino carbonyls in excellent yields via aza-Michael addition of amines to electron deficient alkenes. A remarkable enhancement in the reaction rates was observed with the prepared bifunctional organocatalyst in comparison to the either starch grafted sulfonic acid or the corresponding homogeneous pyridinium p-toluenesulfonate.
Silicon tetrachloride catalyzed aza-michael addition of amines to conjugated alkenes under solvent-free conditions
Azizi, Najmedin,Baghi, Roya,Ghafuri, Hossein,Bolourtchian, Mohammad,Hashemi, Mohammad
experimental part, p. 379 - 382 (2010/04/03)
The efficient and very simple conjugate addition of aromatic and aliphatic amines to α,β-unsaturated carbonyl compounds under solvent-free conditions in the presence of catalytic amount of silicon tetrachloride is reported. The reaction of aryl and alkyl amines with different Michael acceptors gave the corresponding Michael adducts with simple catalyst and good to excellent yields. Georg Thieme Verlag Stuttgart New York.
