71067-27-1Relevant academic research and scientific papers
Cleavage of 1,3-dicarbonyls through oxidative amidation
Biallas, Phillip,H?ring, Andreas P.,Kirsch, Stefan F.
supporting information, p. 3184 - 3187 (2017/04/21)
A mild and convenient protocol for the oxidative cleavage of 1,3-diketone compounds is described. Under metal-free conditions, the method converts the 1,3-dicarbonyls into amides when treated with (nBu4N)N3 and iodine in the presence of an amine at room temperature. Using this method, a range of 1,3-dicarbonyls with various structural motifs including sterically demanding substituents and ordinary functional groups were easily fragmented, and it is demonstrated that cyclic 1,3-dicarbonyls can be directly transformed into acyclic diamides through ring-opening. Initial mechanistic studies show that diazidation of the enol form is followed by nucleophilic substitution with the amine.
Hydrogen bond organocatalysis of benzotriazole in transamidation of carboxamides with amines
Nguyen, Thanh Binh,Ermolenko, Ludmila,Dau, Marie-Elise Tran Huu,Al-Mourabit, Ali
, p. 403 - 416 (2014/01/17)
A new method of transamidation of carboxamides with amines catalyzed by benzotriazole has been developed.
Microwave-assisted preparation of amides using a stable and reusable mesoporous carbonaceous solid acid
Luque, Rafael,Budarin, Vitaly,Clark, James H.,MacQuarrie, Duncan J.
experimental part, p. 459 - 461 (2010/04/22)
An efficient and green microwave assisted protocol to prepare amides from amines via N-acylation using acidic polysaccharide derived mesoporous materials provides quantitative yields of amides in short reaction times.
Formation of carboxamides by direct condensation of carboxylic acids and amines in alcohols using a new alcohol- and water-soluble condensing agent: DMT-MM
Kunishima, Munetaka,Kawachi, Chiho,Hioki, Kazuhito,Terao, Keiji,Tani, Shohei
, p. 1551 - 1558 (2007/10/03)
Selective formation of carboxamides in an alcohol or water by an exceptionally convenient one-step procedure in which a condensing agent is simply added to a mixture of acids and amines has been achieved successfully by using a new condensing agent, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). Activation of carboxylic acids by DMT-MM in the presence of amines and subsequent aminolysis of the resulting acyloxytriazine in alcoholic solvents occurred selectively and led to the formation of carboxamides in excellent yields. The rate of aminolysis of the acyloxytriazine intermediate can be estimated to be about 2×104 times greater than that of methanolysis. The amide/ester selectivity observed using DMT-MM was much larger than that obtained with DCC or EDC. Condensation of polar substrates, such as amino acid esters and their hydrochlorides, glucosamine hydrochloride, sodium acetate and dicarboxylic acids, proceeded successfully in MeOH, water or aqueous MeOH in good yields. The present reaction is technically quite simple and easy to achieve. It proceeds by simple mixing of acids, amines and DMT-MM without any additives, and the MeOH is readily removable by a rotary evaporator after completion of the reaction.
Reactions of amines with N-hydroxy-, N-(2,3-epoxypropoxy)succinimide and naphthalimide
Ranadive, V. B.,Samant, S. D.
, p. 102 - 106 (2007/10/02)
N-Hydroxynaphthalimide (1) and N-hydroxysuccinimide (2) have been prepared. 1 is stable towards alkali, while 2 undergoes hydrolysis at room temperature in the presence of alkali. 1 reacts with amines to form only the salts while 2 reacts with an equivalent amount of primary aliphatic amine to form monoamide of succinamic acid and with an excess of a primary aliphatic amine it forms diamide of succinic acid.It reacts with an aromatic primary amine, irrespective of its concentration, to form only the mono amide of succinamic acid.N-(2,3-Epoxypropoxy)naphthalimide (9) and -succinimide (13) have been prepared from 1 and 2, respectively. 9 on reaction with amines form N-(3-amino-2-hydroxypropoxy)naphthalimides (10). 13 reacts with secondary amines to form 1,3-bisamino-2-propanol, while with aniline it forms N-(3-phenylamino-2-hydroxypropoxy)succinimide.
