91-78-1Relevant academic research and scientific papers
Synthesis and Cytotoxic Activity of Hexahydro-1,3,5-triazine Derivatives through Ring Condensation
Bae, Song Mi,Kang, Sung Young,Song, Ju Hyun
, p. 840 - 846 (2021/03/24)
As a part of a research program for pharmacologically interacting sym-triazine derivatives with hexahydrotriazine ring, novel hexahydrotriazine derivatives (1?13) were successfully synthesized. The synthesis of hexahydrotriazines was carried out from the assembly of three molecules of various amines and three molecules of formaldehyde by “1 + 1 + 1 + 1 + 1 + 1” cycloaddition. The synthesis mechanism is probably passes through imines, which trimerizes to give the hexahydrotriazine ring. All synthesized hexahydrotriazines (1–13) were screened for their cytotoxic activity by cancer cells. As a result, compound 1–9 reduced the viability of T98G cells in a concentration-dependent manner. At a concentration of 100 μM, compound 9 exhibited the greatest cytotoxicity at 94.6%. The reason is that compound 9 is C5H5N that has a resonance hybrid structure and exhibits aromaticity. It is considered to be active because it has a structure that is a raw material for pyridine derivatives as mainly medicines and pesticides.
Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5-Triazinanes with Donor-Acceptor Aziridines and Their Anti-Tumor Activity
Shi, Zhichao,Fan, Tingting,Zhang, Xun,Zhan, Feng,Wang, Zhe,Zhao, Lei,Lin, Jin-Shun,Jiang, Yuyang
supporting information, p. 2619 - 2624 (2021/04/05)
A Y(OTf)3-catalyzed [3+2] cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines. (Figure presented.).
Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation
Cheng, Xiao,Cai, Bao-Gui,Mao, Hui,Lu, Juan,Li, Lei,Wang, Kun,Xuan, Jun
supporting information, p. 4109 - 4114 (2021/05/26)
We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.
Synthesis of α-Amino Tertiary Alkylperoxides by Lewis Acid-Catalyzed Peroxidation of 1,3,5-Triazines
Liu, Lijuan,Shi, Zhichao,Zhang, Xun,Zhan, Feng,Lin, Jin-Shun,Jiang, Yuyang
supporting information, p. 3487 - 3491 (2021/09/20)
α-Substituted peroxides have been found in natural products and are widely used as anti-malarial agents. Zn(OTf)2-catalyzed peroxidation of 1,3,5-triazines has been developed, accessing diversely substituted α-amino tertiary alkylperoxides with high efficiency. Mechanistic investigations and useful synthetic application of the products have also been presented.
Ultrasound-assisted synthesis of substituted triazines and their corrosion inhibition behavior on N80 steel/acid interface
Salman, Mohammad,Ansari, Kashif R.,Haque, Jiyaul,Srivastava, Vandana,Quraishi, Mumtaz A.,Mazumder, Mohammad A. J.
, p. 2157 - 2172 (2020/03/04)
The three substituted triazines were synthesized by ultrasound irradiation method and characterized by FTIR, 13C NMR, and 1H NMR. The corrosion inhibition behavior of the synthesized inhibitors on N80 steel in 15% HCl was studied using electrochemical analyses and weight loss methods. All three inhibitors exhibited excellent corrosion inhibition performance, and the best inhibition effect was shown by TZ-3 (93.2% at 800 mg/L). EIS measurements suggest that the corrosion inhibition process is a charge transfer controlled. The PDP results indicated that all the triazines are mixed-type inhibitors. Langmuir adsorption model is the best fit among the other tested isotherms. These molecules can act as promising acidizing corrosion inhibitors for the oil gas industry. FTIR, AFM, and UV-vis studies corroborate the adsorption of inhibitor molecules over the metal surface.
Aminomethylation of Thioureas with N,N-Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange
McMahon,Sharma,Metta-Maga?a,Pannell
, p. 1764 - 1771 (2020/01/11)
The O-triethylsilylated hemiaminal Et3SiOCH2NMe2 readily transfers the Me2NCH2-group to various thioureas under mild conditions and without catalysts or co-reagents. In the reaction with PhNHC(=S)·NHPh, the initially formed mono-substituted derivative PhNHC(=S)NPhCH2NMe2 readily rearranges to produce the unsymmetrical thiourea PhNHC(=S)NMe2 and hexahydro-1,3,5-triphenyl-1,3,5-triazine.
Iridium-catalyzed 1,5-(aryl)aminomethylation of 1,3-enynes by alkenyl-to-allyl 1,4-iridium(i) migration
Ruscoe, Rebecca E.,Callingham, Michael,Baker, Joshua A.,Korkis, Stamatis E.,Lam, Hon Wai
supporting information, p. 838 - 841 (2019/01/21)
A novel multicomponent coupling reaction involving the iridium-catalyzed 1,5-difunctionalization of 1,3-enynes with arylboronic acids and triazinanes is described. A key step in this 1,5-(aryl)aminomethylation reaction is the alkenyl-to-allyl 1,4-iridium(i) migration.
Activation Relay on Rhodium-Catalyzed C-H Aminomethylation in Cooperation with Photoredox Catalysis
Liu, Ruixing,Liu, Jiaxin,Wei, Yin,Shi, Min
supporting information, p. 4077 - 4081 (2019/06/14)
A site selective C-H aminomethylation at indole's C3 position has been achieved by merging rhodium(III)-catalyzed C-H activation and photoredox catalysis in a one-pot manner. An investigation of the mechanistic insights rationalized the essence of the activation relay and the combination mode.
Vinylethylene Carbonates as α,β-Unsaturated Aldehyde Surrogates for Regioselective [3 + 3] Cycloaddition
Xu, Yi,Chen, Lu,Yang, Yu-Wen,Zhang, Zhiqiang,Yang, Weibo
supporting information, p. 6674 - 6678 (2019/09/03)
Herein, we report a novel stepwise addition-controlled ring size method, to access tetrahydropyrimidines through an operationally simple [3 + 3] cycloaddition of vinylethylene carbonates with triazinanes. Interestingly, we could also use this method for a [3 + 3] oxidative cycloaddition, which allows the facile synthesis of polysubstituted terphenyls under mild conditions. Mechanistic studies suggest that vinylethylene carbonates could generate α,β-unsaturated aldehydes as 3-carbon synthons for cycloaddition via a combination process of Pd-catalyzed decarboxylation and β-H elimination.
Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines: Via copper(i)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines
Zhou, Yuxuan,Ma, Fanghui,Lu, Ping,Wang, Yanguang
supporting information, p. 8849 - 8852 (2019/10/28)
We report a facile and efficient synthesis of spiro[imidazolidine-4,3′-indolin]-2′-imines via a copper(i)-catalyzed cascade reaction of 3-diazoindolin-2-imines with 1,3,5-triazines. The reaction proceeds under very mild conditions and tolerates a variety of functional groups. The cascade process involves the formation of a copper-carbene intermediate and a formal [2 + 2 + 1] cycloaddition.
