612095-65-5Relevant academic research and scientific papers
Synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid
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Paragraph 0047-0049, (2020/07/13)
The invention relates to a synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid. The preparation method is characterized by comprising the following steps: weighing organic carboxylic acid, organic amine, niobium pentachloride, ionic liquid and a molecular sieve, adding the materials into a reactor, adding an organic solvent, and reacting for 6-24 hours at the reaction temperature of 70-110 DEG C to obtain a corresponding amide product. The molar ratio of the organic carboxylic acid to the organic amine to the niobium pentachloride to the ionic liquid is 1:(1-3):(0.01-1):(0.05-1); wherein the mass ratio of the organic carboxylic acid to the molecular sieve is 1: (0.2-1). According to the method, the substrate range is expanded, the reaction yield is high (95% or above), the catalyst dosage is small, the atom economy is high, the catalyst is cheap and easy to obtain, the production cost can be greatly reduced, and the method is suitable for industrial production.
Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid
Ghosh, Santanu,Jana, Chandan K.
, 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.
NHC-catalyzed C-O or C-N bond formation: Efficient approaches to α,β-unsaturated esters and amides
Zhang, Bo,Feng, Peng,Cui, Yuxin,Jiao, Ning
, p. 7280 - 7282 (2012/07/28)
Simple and efficient NHC-catalyzed transformations of bromoenal or α,β-dibromoenal into α,β-unsaturated esters or amides with high stereoselectivity through C-O or C-N bond formation have been demonstrated. The NHC-catalyzed processes occur under mild con
Oxidation of aliphatic α,β-unsaturated aldimines to amides specifically by oxone with AlCl3
Lu, Zhou,Peng, Lijun,Wu, Wentao,Wu, Longmin
, p. 2357 - 2366 (2008/09/21)
α,β-Unsaturated aldimines were specifically oxidized to amides with Oxone in the presence of AlCl3 as a Lewis acid in CH2Cl2. No migration of aryl group occurred in the rearrangement reaction. Copyright Taylor & Francis Group, LLC.
Some chemical properties of 2,3-dihydro-4H-[1,3]thiazino[3,2-a] benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4- ones
Britsun,Esipenko,Lozinskii
, p. 396 - 402 (2008/02/04)
We have studied the reaction of 2,3-dihydro-4H-[1,3]thiazino[3,2-a] benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4- ones with amines, alkylating reagents, and hydrogen peroxide. We have shown that the presence of an aryl substituent at the 2 position of [1,3-thiazino[3,2-a] benzimidazol-4-ones has a substantial effect on the direction of the reactions. 2006 Springer Science+Business Media, Inc.
An atom efficient and solvent-free synthesis of structurally diverse amides using microwaves
Gelens, Edith,Smeets, Luc,Sliedregt, Leo A.J.M.,Van Steen, Bart J.,Kruse, Chris G.,Leurs, Rob,Orru, Romano V.A.
, p. 3751 - 3754 (2007/10/03)
An array of structurally diverse amides was synthesized efficiently by combining (primary and secondary) amines and carboxylic acids in one-pot under solvent-free microwave (MW) conditions. In most cases, no racemization was observed with optically active inputs and chiral amides were obtained in high ee or de.
A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral dioxirane-mediated catalytic asymmetric epoxidation of cinnamic acid derivatives
Imashiro, Ritsuo,Seki, Masahiko
, p. 4216 - 4226 (2007/10/03)
A novel and practical asymmetric synthesis of chiral glycidic acid derivatives involving methyl (2R,3S)-3-(4-methoxyphenyl)glycidate ((2R,3S)-2a), a key intermediate for diltiazem hydrochloride (1), was developed. Treatment of methyl (E)-4-methoxycinnamate ((E)-3a) with chiral dioxirane, generated in situ from a catalytic amount (5 mol %) of an 11-membered C2-symmetric binaphthyl ketone (R)-7a, provided (2R,3S)-2a in 92% yield and 80% ee. Other cinnamic acid esters and amides were epoxidized by the use of the same procedure to give the corresponding chiral glycidic acid derivatives with up to 95% yield and 92% ee. Higher enantioselectivities in the asymmetric epoxidation of (E)-cinnamates than that of (E)-stilbene derivatives were observed and were proposed to be attributed to a dipole-dipole repulsion between oxygen atoms of an ester group in the cinnamates and those of the lactone moieties in the binaphthyl dioxirane.
Synthesis of β-monosubstituted α,β-unsaturated amides with z-selectivity using diphenylphosphonoacetamides
Kojima, Satoshi,Hidaka, Tsugihiko,Ohba, Yuko
, p. 515 - 523 (2007/10/03)
The utility of diphenylphosphonoacetamides [(PhO)2P(O)CH 2CONRR′] as Horner-Wadsworth-Emmons reagents was examined with five different patterns of substitution upon the amide nitrogen atom (2a: R, R′ = CH2Ph; 2b: R = CH2Ph, R′ = H; 2c: R = Me, R′ = OMe; 2d: R, R′ = Ph; 2e: R, R′ = (CH2) 4). The reaction of 2a was found to be Z-selective for aromatic aldehydes with selectivities up to 95:5. Reagent 2b led to reasonable selectivity for both benzaldehyde (85:15) and 3-phenylpropionaldehyde (87:13), while 2c was somewhat effective for only the latter alkyl aldehyde (83:17). Compounds 2d and 2e exhibited slightly lower selectivities compared with 2a.
