4269-30-1Relevant articles and documents
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.
On-water magnetic NiFe2O4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
Payra, Soumen,Saha, Arijit,Banerjee, Subhash
, p. 95951 - 95956 (2016/10/25)
Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C-C and C-X (X = N, S, O etc.) bond through 1,4-addition reactions.
Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions
Tamaddon, Fatemeh,Tayefi, Mohammad,Hosseini, Elaheh,Zare, Elham
, p. 36 - 42 (2013/02/22)
Iranian dolomite (CaMg(CO3)2) which consists of double-layered carbonates with Ca2+ and Mg2+ ions was utilized as a heterogeneous base catalyst in the CC, CN, and CS bond forming reactions via the Henry, Knoevenagel, aza-Michael, and thia-Michael transformations under mild conditions in water. Iranian dolomite has been characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer Emmett Teller (BET) and XRF chemical analysis, while its basic strength was evaluated by following the Hammett indicators procedure. This water-insoluble natural catalyst demonstrated high activity and was reusable.
Accelerated C-N bond formation in dropcast thin films on ambient surfaces
Badu-Tawiah, Abraham K.,Campbell, Dahlia I.,Cooks, R. Graham
, p. 1461 - 1468,8 (2020/08/24)
The aza-Michael addition and the Mannich condensation occur in thin films deposited on ambient surfaces. The reagents for both C-N bond formation reactions were transferred onto the surface by drop-casting using a micropipette. The surface reactions were
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.
Microwave-assisted, rapid, solvent-free aza-michael reaction by perchloric acid impregnated on silica gel
Singh, Surya Prakash,Kumar, T. Vijaya,Chandrasekharam,Giribabu,Reddy, P. Yella
experimental part, p. 3982 - 3989 (2009/12/24)
Highly efficient solvent-free aza-Michael additions of a variety of amines to,-unsaturated carbonyl compounds under microwave-irradiation conditions catalyzed by perchloric acid impregnated on silica gel (HClO4/SiO2) is reported. The reactions are completed within 2-7min in a microwave oven to produce the corresponding adducts in excellent yields, and the catalyst can be recovered and reused.
SUBSTITUTED PYRROLIDINE AND PIPERIDINE COMPOUNDS, DERIVATIVES THEREOF, AND METHODS FOR TREATING PAIN
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Page/Page column 77-78, (2009/10/22)
The present application relates to pyrrolidine, piperidine, and other nitrogen-containing heterocyclic derivatives and the use of these compounds for treating and preventing pam or inflammation. The analgesic compounds demonstrate efficacy in the treatment of neuropathic pain resulting from a variety of conditions such as diabetic neuropathy, HIV infections, and post-herpetic neuralgia.
Silica gel accelerated aza-Michael addition of amines to α,β-unsaturated amides
You, Lisha,Feng, Song,An, Rui,Wang, Xinhong,Bai, Donglu
, p. 5147 - 5149 (2008/12/20)
A novel method to synthesize β-amino amide has been developed via conjugated addition of amine to bulky α,β-unsaturated amides promoted by silica gel. The silica gel worked efficiently to accelerate the reaction and afforded the related adduct in good to excellent yield.