156732-93-3Relevant articles and documents
New Strategy for the Synthesis of Heterocycles via Copper-Catalyzed Oxidative Decarboxylative Amination of Glyoxylic Acid
Niu, Bin,Li, Shaoqing,Cui, Chang,Yan, Yizhe,Tang, Lin,Wang, Jianyong
, p. 7800 - 7803 (2019)
A copper-catalyzed oxidative decarboxylative amination of glyoxylic acid with substrates having two nitrogen-nucleophilic sites was first demonstrated. Using this novel approach, 1,3,5-triazines, quinazolinones and quinazolines were obtained in up to 93 % yields. Notably, glyoxylic acid was employed as the C1 synthon for heterocycles. This strategy enriches the application of glyoxylic acid for the synthesis of valuable heterocycles.
Synthesis of 1,2-dihydro-1,3,5-triazine derivativesviaCu(ii)-catalyzed C(sp3)-H activation ofN,N-dimethylethanolamine with amidines
Chen, Rener,Ma, Renchao,Ma, Yongmin,Wang, Lei,Wang, Zhiming,Yan, Min
supporting information, p. 10946 - 10949 (2020/10/02)
1,2-Dihydro-1,3,5-triazines and symmetrical 1,3,5-triazines were obtained in up to 81% yields from amidines andN,N-dimethylethanolamine catalyzed by CuCl2. The reaction involves three C-N bond formations during the oxidative annulation process
Dichloromethane as C1 Building Block: Synthesis of 2,4-Disubstitued 1,3,5-Triazines via Copper-Catalyzed Aerobic C?H/C?Cl Cleavage
Yan, Yizhe,Cui, Chang,Wang, Jianyong,Li, Shaoqing,Liu, Yanqi
supporting information, p. 1166 - 1170 (2019/01/30)
A copper-catalyzed aerobic oxidative annulation of amidines with dichloromethane was first demonstrated. Using this novel approach, 16 examples of symmetrical 2,4-disubstitued 1,3,5-triazines and 7 examples of unsymmetrical ones were obtained with up to 82% yields. Moreover, a D-labeling experiment proved that dichloromethane was employed as the C1 building block and solvent. A primary kinetic isotope effect revealed that the C?H cleavage of dichloromethane might be a rate-determining step. This protocol provides a novel strategy for the synthesis of heterocycles. (Figure presented.).
Transition metal-free assembly of 1,3,5-triazines using ethyl bromodifluoroacetate as C1 source
Yu, Xiaoxia,Zhou, Yao,Ma, Xingxing,Song, Qiuling
supporting information, p. 8079 - 8082 (2019/07/15)
An efficient transition metal-free annulation of amidine with ethyl bromodifluoroacetate to access 2,4-disubstituted-1,3,5-triazines is firstly presented. The desired symmetric and unsymmetric 2,4-disubstituted-1,3,5-triazines were obtained in decent yields via multiple C-N bond formation, in which ethyl bromodifluoroacetate is harnessed as a unique C1 synthon via quadruple cleavage. This reaction is transition metal-free, oxidant-free and simple in operation, and only lowly toxic inorganic wastes are generated.
An I2-mediated aerobic oxidative annulation of amidines with tertiary amines: Via C-H amination/C-N cleavage for the synthesis of 2,4-disubstituted 1,3,5-triazines
Yan, Yizhe,Li, Zheng,Cui, Chang,Li, Hongyi,Shi, Miaomiao,Liu, Yanqi
supporting information, p. 2629 - 2633 (2018/04/27)
An iodine-mediated formal oxidative cycloaddition of amidines with tertiary amines was first demonstrated in air. Both symmetrical and unsymmetrical 2,4-disubstituted 1,3,5-triazines were obtained in up to 85% yields. It is noted that a tertiary amine was employed as a one carbon synthon of 1,3,5-triazines and two C-N bonds were formed in one pot. Control experiments revealed that the reaction underwent a radical pathway promoted by I+. The method is transition-metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates.
Silver-catalyzed [3+2+1] annulation of aryl amidines with benzyl isocyanide
Lu, Xiaodong,Xin, Xiaoyi,Wan, Boshun
, p. 361 - 364 (2018/01/08)
A silver-catalyzed [3+2+1] annulation of amidines with benzyl isocyanide toward 2,4-diaryl-1,3,5-triazines was developed. A variety of symmetrical and unsymmetrical products were obtained in moderate to good yields. This work also features an oxidant-free approach to 2,4-disubstituted triazines.
Alkyl Ether as a One-Carbon Synthon: Route to 2,4-Disubstituted 1,3,5-Triazines via C-H Amination/C-O Cleavage under Transition-Metal-Free Conditions
Yan, Yizhe,Li, Zheng,Li, Hongyi,Cui, Chang,Shi, Miaomiao,Liu, Yanqi
supporting information, p. 6228 - 6231 (2017/11/24)
A transition-metal-free oxidative formal [3 + 2 + 1] cycloaddition for the synthesis of symmetrical and unsymmetrical 2,4-disubstituted 1,3,5-triazines has been first demonstrated. The reaction is involved in a domino C-H amination of alkyl ethers with amidines, C-O cleavage, nucleophilic addition, condensation, and an oxidative aromatization process. Notably, two C-N bonds were constructed in one pot, and alkyl ethers were employed as a novel carbon source of 1,3,5-triazines. The preliminary mechanistic studies revealed the reaction underwent a radical pathway.
Preparation method for 2,4-disubstituted-1,3,5-triazine derivatives
-
Paragraph 0017; 0020; 0048; 0049; 0051, (2017/07/20)
The invention relates to a preparation method for symmetric and asymmetric 2,4-disubstituted-1,3,5-triazine derivatives. Specifically, substituted amidine reacts with benzyl isocyanide under the catalysis of a silver salt or copper salt so as to produce t
Copper-Catalyzed Oxidative C(sp3)-H Functionalization for Facile Synthesis of 1,2,4-Triazoles and 1,3,5-Triazines from Amidines
Huang, Huawen,Guo, Wei,Wu, Wanqing,Li, Chao-Junx,Jiang, Huanfeng
supporting information, p. 2894 - 2897 (2015/06/30)
A facile and versatile catalytic system involving copper catalyst, K3PO4 as the base, and O2 as the oxidant has been developed to enable efficient synthesis of 2,4,6-trisubstituted and 2,6-disubstituted 1,3,5-triazines and
