83304-16-9Relevant academic research and scientific papers
Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
álvarez-Pérez, Andrea,Esteruelas, Miguel A.,Izquierdo, Susana,Varela, Jesús A.,Saá, Carlos
supporting information, p. 5346 - 5350 (2019/07/08)
Complex CpRuCl(PPh3)2 catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(=C=CHR)(PPh3)2]+ which are oxidized to the Ru(η2-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.
Microwave-assisted amidation of arylacetic acids by reaction with 2-aryl-ethylamines
Gruen, Alajos,Milen, Matyas,Foeldesi, Tamas,Abranyi-Balogh, Peter,Drahos, Laszlo,Keglevich, Gyoergy
, p. 1491 - 1498 (2013/05/21)
Twenty-five amides were synthesized in almost quantitative yields by microwaveassisted condensation of arylacetic acids and 2-aryl-ethylamines under solventless conditions. The N-arylethyl-arylacetylamides are intermediates of the corresponding isoquinoli
Development of chlorotriazine polymer dehydrocondensing reagents (Poly-Trzs)
Kunishima, Munetaka,Yamamoto, Kazuyoshi,Hioki, Kazuhito,Kondo, Tomohito,Hasegawa, Masumi,Tani, Shohei
, p. 2604 - 2612 (2007/10/03)
Polymer-type dehydrocondensing reagents comprising of a triazine dehydrocondensing reagent, itself in a polymerized form (Poly-Trz-MMs'), have been developed by exploiting the chemical properties of cyanuric chloride that readily binds to alcohol or amines. A chlorotriazine polymer bearing two alkoxy substituents at the 4- and 6- positions (Poly-O-Trz-Cl) was prepared by alternating copolymerization between cyanuric chloride and tetra(ethylene glycol). Similarly, polymers bearing both alkoxy and amino substituents (Poly-N-Trz-Cl) were synthesized from tetra(ethylene glycol) bis(4,6-dichlorotriazin-2-yl) ether 6 and tris(2-aminoethyl)amine 7 and/or ethylenediamine 8. All the polymers were shown to be good reagents for dehydrocondensation of carboxylic acids and amines in the presence of NMM, compared to the corresponding monomeric dehydrocondensing reagent (DMT-MM). The advantages of the polymeric reagents are as follows: (1) both the reaction and isolation procedure of dehydrocondensation can be greatly simplified, (2) the dehydrocondensation can be conducted in protic solvents as well as in common organic solvents, (3) the reagents can be efficiently prepared at a low cost, and (4) these reagents are considered eco-friendly, generating a lower amount of waste compared to conventionally related reagents because of high loading of the dehydrocondensing activity (ca. 3 mequiv/g).
Antileukotrienic N-arylethyl-2-arylacetamides in the treatment of ulcerative colitis
Junek, Richard,Brunova, Bohumila,Kverka, Miloslav,Panajotova, Vladimira,Jandera, Antonin,Kuchar, Miroslav
, p. 1084 - 1094 (2008/03/13)
A series of arylacetic acid derivatives bearing methyl(arylethyl)amino groups were prepared and their antileukotrienic activities involving LTB4 were evaluated. Regression analysis has shown a strong dependence of these activities on lipophilic
Development of novel polymer-type dehydrocondensing reagents comprised of chlorotriazines
Kunishima, Munetaka,Yamamoto, Kazuyoshi,Watanabe, Yasunobu,Hioki, Kazuhito,Tani, Shohei
, p. 2698 - 2700 (2007/10/03)
A novel immobilized dehydrocondensing reagent comprised of a triazine-type dehydrocondensing reagent itself in a polymerized form was synthesized by copolymerization between tetra(ethylene glycol) bis(dichlorotriazinyl) ether and tris(2-aminoethyl)amine.
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.
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride: An efficient condensing agent leading to the formation of amides and esters
Kunishima, Munetaka,Kawachi, Chiho,Morita, Jun,Terao, Keiji,Iwasaki, Fumiaki,Tani, Shohei
, p. 13159 - 13170 (2007/10/03)
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) was quantitatively synthesized by the coupling of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N- methylmorpholine (NMM) in THF, and characterized. Condensation of carboxylic acids and amines by DMTMM proceeded effectively in THF to give the corresponding amides in good yields. The corresponding esters can be obtained by esterification of carboxylic acids with DMTMM in methanol, ethanol, isopropyl alcohol, or t-butyl alcohol in the presence of NMM. The amount of alcohols can be reduced to a stoichiometric amount by conducting the reaction in THF. Since the reactions proceed under atmospheric conditions without drying of the solvent, and the co- product (4,6-dimethoxy-1,3,5-triazin-2(1H)-one) arising from DMTMM after condensation can be readily removed by extraction, this method is a very practical one.
Synthesis and Photo-oxygenation of Some Substituted 1-Benzyl-3,4-dihydroisoquinolines. Mechanism of Enamine Photo-oxygenation
Martin, Ned H.,Jefford, Charles W.
, p. 762 - 774 (2007/10/02)
The synthesis of a series of substituted 1-benzyl-3,4-dihydroisoquinolines by Bischler-Napieralski cyclization is described.Competitive methylene blue sensitized photo-oxygenation experiments allowed the determination of relative rates of photo-oxygenation of 1-benzyl-3,4-dihydroisoquinolines.Substituents were shown to affect both the equilibrium concentration of the tautomeric enamine and the overall photo-oxygenation rate.After correcting for differences in enamine concentration, the relative rate data provided a diagnostic probe of the reaction mechanism, which involves transfer of charge in the rate-limiting step.
