6328-77-4Relevant academic research and scientific papers
3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed metal-free amide bond formation from thioacids and amines at room temperature
Samanta, Suvendu,Ray, Shounak,Bhaduri, Samanka Narayan,Samanta, Partha Kumar,Biswas, Papu
supporting information, (2020/08/10)
A 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed efficient, mild and metal-free method has been developed for direct amide bond synthesis from simple thioacids and amines as starting materials. This methodology is useful for aromatic, aliphatic, and heteroaromatic thioacids as well as primary, secondary, heterocyclic, and even functionalized amines. A wide substrates scope, operationally mild conditions, and acylation of amines without affecting other functional groups such as alcohols, esters, carbodithioates, among others make this strategy very attractive and practical.
Solvent- and transition metal-free amide synthesis from phenyl esters and aryl amines
Rzhevskiy, Sergey A.,Ageshina, Alexandra A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
, p. 1536 - 1540 (2019/01/24)
A general, economical, and environmentally friendly method of amide synthesis from phenyl esters and aryl amines was developed. This new method has significant advantages compared to previously reported palladium-catalyzed approaches. The reaction is performed transition metal- and solvent-free, using a cheap and environmentally benign base, NaH. This approach enabled us to obtain target amides in high yields with high atom economy.
Peroxide-mediated direct synthesis of amides from aroyl surrogates
Hong, Gang,Wu, Shengying,Zhu, Xiaoyan,Mao, Dan,Wang, Limin
, p. 436 - 441 (2015/12/31)
An efficient and metal-free method has been developed for the direct synthesis of amides from readily available azobenzenes reacting with aroyl surrogates such as alcohols, methylarenes. A variety of amides were afforded in moderate to good yields through this reaction. It is another example reported by our group for the use of azobenzene as the new radical acceptor.
Para-Selective C-H Amidation of Simple Arenes with Nitriles
Xiang, Shi-Kai,Li, Jin-Mei,Huang, He,Feng, Chun,Ni, Hai-Liang,Chen, Xiao-Zhen,Wang, Bi-Qin,Zhao, Ke-Qing,Hu, Ping,Redshaw, Carl
supporting information, p. 3435 - 3440 (2016/01/25)
A para-selective C-H amidation of simple arenes with nitriles has been developed. By increasing the amount of arenes, a further meta-selective C-H arylation of the produced amides occurred. Both steric and electronic effects are utilized to control the selectivity, resulting in only para-selective amidation products. The readily available nitriles as amidation reagents instead of amides makes the synthesis of N-arylamides more accessible.
Decomposition of benzoylthioureas into benzamides and thiobenzamides under solvent-free conditions using iodine-alumina as the catalyst and its mechanistic study by density functional theory
Nahakpam, Lokendrajit,Chipem, Francis A. S.,Chingakham, Brajakishor S.,Laitonjam, Warjeet S.
supporting information, p. 2240 - 2247 (2015/03/18)
The breaking down of benzoylthioureas to benzamides and thiobenzamides in a single route using iodine-alumina as the catalyst under solvent-free conditions is highlighted. Results show that when an electron donating group, such as the methyl or methoxy group, is at the para-position of the aryl group of 1, benzamide (2) is the favoured product. When an electron withdrawing group, such as the chlorine or nitro group, is at the para-position of the aryl group of 1, thiobenzamide (3) is the favoured product. From the study of the reaction mechanism, it may be postulated that the formation of benzamide is due to the migration of the aryl group, whereas the formation of thiobenzamide may be due to the migration of the phenyl group. Thus, a new method for the formation of benzamides and thiobenzamides was developed.
Copper-catalyzed selective benzylic C-O cyclization of N-o-tolylbenzamides: Synthesis of 4 H-3,1-benzoxazines
Li, Yan,Li, Zhongshu,Xiong, Tao,Zhang, Qian,Zhang, Xiangyang
supporting information; body text, p. 3522 - 3525 (2012/08/08)
A novel Selectfluor-mediated copper-catalyzed highly selective benzylic C-O cyclization for the synthesis 4H-3,1-benzoxazines is reported. The predominant selectivity for a benzylic C(sp3)-H over an aromatic C(sp 2)-H bond in N-o-tolylbenzamides is achieved.
Efficient copper-catalyzed N-arylation of amides and imidazoles with aryl iodides
Ali, Md. Ashif,Saha, Prasenjit,Punniyamurthy, Tharmalingam
supporting information; experimental part, p. 908 - 910 (2010/04/29)
The C-N cross-coupling of amides and imidazoles with aryl iodides is described using CuI in tetrabutylammonium bromide (TBAB) under ligand-free conditions. The reaction is simple, general, and efficient affording the C-N cross-coupled products in shorter time and in high yield. Georg Thieme Verlag Stuttgart ? New York.
Reusable Cu2O-nanoparticle-catalyzed amidation of aryl iodides
Jammi, Suribabu,Krishnamoorthy, Sankarganesh,Saha, Prasenjit,Kundu, Dipti S.,Sakthivel, Sekarpandi,Ali, Md Ashif,Paul, Rajesh,Punniyamurthy, Tharmalingam
experimental part, p. 3323 - 3327 (2010/03/03)
The amidation of aryl iodides using Cu2O nanoparticles is described. It is a heterogeneous process, no leaching of the Cu2O species occurs, and the catalyst can be recovered and recycled without loss of activity. Georg Thieme Verlag Stuttgart - New York.
N-Acyltetrazole as an intermediate for preparation of carboxylic acid derivatives
Jursic
, p. 361 - 364 (2007/10/02)
A new mild and very efficient procedure for preparation of acid derivatives via N-acyl-5-phenyltetrazole is reported. The yields are high at -10°C and purification is simple but, because of the thermal instability of the intermediate, a certain amount of corresponding oxadiazole arises if the reaction is carried out at higher temperature.
