55643-77-1Relevant academic research and scientific papers
Synthesis, photophysical and redox properties of the 2,5,7-tri(het)aryl- [1,2,4]triazolo[1,5-a]pyrimidines
Charushin, Valery N.,Chupakhin, Oleg N.,Demina, Nadezhda S.,Irgashev, Roman A.,Rasputin, Nikolay A.,Rusinov, Gennady L.,Shchepochkin, Alexander V.
, (2020/10/30)
A number of Y-type push-pull compounds based on the [1,2,4]triazolo[1,5-a]pyrimidine core, namely 5,7- di(het)aryl-substituted 2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidines, were obtained by transition metal free nucleophilic C-H functionalization. Substituents at both the C-5 and C-7 positions were introduced by successive treatment of the starting 6-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine with Grignard reagents. In addition, the optical and electrochemical properties of the synthesized push-pull systems were studied.
Trichloroisocyanuric acid-mediated synthesis of 1,5-fused 1,2,4-triazoles from N-heteroaryl benzamidines via intramolecular oxidative N–N bond formation
Bhatt, Ashish,Singh, Rajesh K.,Sarma, Bhupendra K.,Kant, Ravi
supporting information, (2019/08/13)
A convenient synthesis of 1,5-fused 1,2,4-triazoles from readily available N-heteroaryl benzamidines is reported. The reaction is efficiently promoted by trichloroisocyanuric acid to afford the desired products, mostly in high yields and in relatively sho
A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N-N Bond Formation
Bhatt, Ashish,Kant, Ravi,Sarma, Bhupendra K.,Singh, Rajesh K.
, p. 3883 - 3890 (2019/10/11)
A convenient synthesis of 1,5-fused 1,2,4-triazoles from readily available N-arylamidines is reported. The reaction is efficiently promoted by chloramine-T to afford the desired products mostly in high yields and in relatively short time, through direct m
Molecular Engineering of Mechanochromic Materials by Programmed C-H Arylation: Making a Counterpoint in the Chromism Trend
Wu, Jie,Cheng, Yangyang,Lan, Jingbo,Wu, Di,Qian, Shengyou,Yan, Lipeng,He, Zhen,Li, Xiaoyu,Wang, Kai,Zou, Bo,You, Jingsong
supporting information, p. 12803 - 12812 (2016/10/13)
The development of facile methods for screening organic functional molecules through C-H bond activation is a revolutionary trend in materials research. The prediction of mechanochromism as well as mechanochromic trends of luminogens is an appealing yet challenging puzzle. Here, we present a strategy for the design of mechanochromic luminogens based on the dipole moment of donor-acceptor molecules. For this purpose, a highly efficient route to 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines (2,7-diaryl-TAPs) has been established through programmed C-H arylation, which unlocks a great opportunity to rapidly assemble a library of fluorophores for the discovery of mechanochromic regularity. Molecular dipole moment can be employed to explain and further predict the mechanochromic trends. The 2,7-diaryl-TAPs with electron-donating groups on the 2-aryl and electron-withdrawing groups on the 7-aryl possess a relatively small dipole moment and exhibit a red-shifted mechanochromism. When the two aryls are interchanged, the resulting luminogens have a relatively large dipole moment and display a blue-shifted mechanochromism. Seven pairs of isomers with opposite mechanochromic trends are presented as illustrative examples. The aryl-interchanged congeners with a bidirectional emission shift are structurally similar, which provides an avenue for understanding in-depth the mechanochromic mechanism.
I2/KI-Mediated Oxidative N-N Bond Formation for the Synthesis of 1,5-Fused 1,2,4-Triazoles from N -Aryl Amidines
Song, Lina,Tian, Xianhai,Lv, Zhigang,Li, Ertong,Wu, Jie,Liu, Yangxue,Yu, Wenquan,Chang, Junbiao
, p. 7219 - 7225 (2015/07/28)
An I2/KI-mediated oxidative N-N bond formation reaction is described. This new and environmentally benign approach allows for the convenient synthesis of a variety of 1,2,4-triazolo[1,5-a]pyridines and other 1,5-fused 1,2,4-triazoles from readi
Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles [1]
Al-Awadi, Sundus A.,Ibrahim, Maher R.,El-Dusouqui, Osman M. E.,Al-Awadi, Nouria A.
, p. 1812 - 1816 (2015/11/09)
Gas-phase pyrolysis of N-arylidine-N′-pyrimidin-2-yl-hydrazine derivatives 1a, 1b, 1c, 1d, 1e gave the corresponding arylnitriles 2a, 2b, 2c, 2d, 2e, 2-aminopyrimidine 3, 3-phenyl-1,2,4-triazolo[4,3-a]pyrimidines 4, 2-phenyl-1,2,4-triazolo[1,5-a]pyrimidines 5, 2,4,5-triphenyl-1H-imidazole 6, and 2,3-diphenylquinoline 7. The analyses of the reaction products are reported and used to elucidate the mechanism of the pyrolytic process.
Synthesis of 2-Aryl-1,2,4-triazolopyrimidines
Prasad, V.S.R.,Reddy, K.Kondal
, p. 2617 - 2622 (2007/10/02)
N-2-Pyrimidylarylamidines (2) obtained by the reaction of 2-aminopyrimidines (1) with aryl cyanides in the presence of anhydrous aluminium chloride have been converted into 2-aryl-1,2,4-triazolopyrimidines (4) by oxidative cyclisation in the presence of lead tetraacetate.
Synthesis of 2-Aryltriazolopyrimidines
Kamala, K.,Rao, P. Jayaprasad,Reddy, K. Kondal
, p. 3791 - 3793 (2007/10/02)
2-Aroylamino)pyrimidines (4) have been converted into 1-(2-pyrimidyl)-5-aryl-1H-tetrazoles (6) by treatment with PCl5 followed by azidolysis in aqueous acetone solution.Pyrolysis of 6 in decalin gave 2-aryltriazolopyrimidines (8).A reasonable pathway for the formation of 8 from 6 is suggested.Structures of all the compounds have been established by elemental analysis and spectral data.
