6639-47-0Relevant articles and documents
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.
3, 4-dihydro-2H-1, 3-thiazine derivative and preparation method thereof
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Paragraph 0030, (2020/11/12)
The invention belongs to the field of chemical synthesis, and particularly relates to a 3, 4-dihydro-2H-1, 3-thiazine derivative and a preparation method thereof. The structural formula of the 3, 4-dihydro-2H-1, 3-thiazine derivative is shown in the speci
Aminomethyl Transfer (Mannich) Reactions Between an O-Triethylsilylated Hemiaminal and Anilines, RnC6H5?nNH2 Leading to New Diamines, Triamines, Imines, or 1,3,5-Triazines Dependent upon Substituent R
Jacintomoreno, Anwar,Sharma, Hemant K.,Metta-Maga?a, Alejandro,Pannell, Keith H.
, p. 11302 - 11307 (2019/08/20)
The reactions of the Mannich reagent Et3SiOCH2NMe2 (1) with a variety of anilines (mono-substituted RC6H4NH2, R=H, 4-CN, 4-NO2, 4-Ph, 4-Me, 4-MeO, 4-Me2N; di-substituted R2C6H3NH2, R2=3,5-(CH3)2, 3,5-(CF3)2; tri-substituted R3C6H2NH2, R3=3,5-Me2-4-Br and a “super bulky” aniline (Ar*NH2) [Ar=2,6-bis(diphenylmethyl)-4-tert-butylphenyl]) led to the formation of a range of products dependent upon the substituent. With electron-withdrawing substituents, previously unknown diamines, RC6H4NH(CH2NMe2) [R=CN (2 a), NO2 (2 b)] and R2C6H3NH(CH2NMe2) [R2=3,5-(CF3)2 (2 c)] were formed. Further reaction of 2 a, b, c with 1 yielded the corresponding triamines RC6H4N(CH2NMe2)2 (R=CN (3 a), NO2 (3 b) and R2C6H3N(CH2NMe2)2, R2=3,5-(CF3)2 (3 c). The new polyamines were characterized by NMR spectroscopy, and for 2 a, 2 c, and 3 c, by single crystal XRD. In the case of electron-donating groups, R=4-OMe, 4-NMe2, 4-Me, 3,5-Me2, 3,5-Me2-4-Br, and for R=4-Ph, the reactions with 1 immediately led to the formation of the related 1,3,5-triazines, R=4-MeO (5 a), 4-Me2N (5 b), 4-Me (5 c), 3,5-Me2 (5 d), 3,5-Me2-4-Br (5 e), 4-Ph (5 f), 4-Cl (5 g). The “super bulky” aniline rapidly produced a single product, namely the corresponding imine Ar*N=CH2 (4) which was also characterized by single crystal XRD. Imine 4 is both thermally and oxidatively stable. All reactions are very fast, thus based upon the presence of Si we are tempted to denote the reactions of 1 as examples of “Silick” chemistry.
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.
Synthesis, molecular structure, conformation and biological activity of Ad-substituted N-aryl-tetraoxaspiroalkanes
Tyumkina, Tatyana V.,Makhmudiyarova, Nataliya N.,Kiyamutdinova, Guzeliya M.,Meshcheryakova, Ekaterina S.,Bikmukhametov, Kamil Sh.,Abdullin, Marat F.,Khalilov, Leonard M.,Ibragimov, Askhat G.,Dzhemilev, Usein M.
, p. 1749 - 1758 (2018/03/07)
An efficient method has been developed for the synthesis of 7′-arylspiro{adamantane-[2,3′]-(1′,2′,4′,5′,7′-tetraoxazocanes)} by the ring transformation reaction of spiro{adamantane-[2,3’]-(1′,2′,4′,5′,7′-pentaoxacane)} with arylamines in the presence of S
Synthesis of hexahydro-symtriazines using PEG-400 as superior solvent
Bondle, Giribala M.,Jadhav, Rohit G.,Kamble, Vinod T.,Atkore, Sandeep T.
, p. 18 - 23 (2017/03/06)
1,3,5-Hexahydrotriazine derivatives show broad spectrum of biological activities such as anticancer, antitumor. Some of their derivatives are used as carcenolytics, herbicides and show antidote and growth stimulating activities. Very few methodologies are reported for the synthesis of symtriazines. Synthesis of trimer of hexahydrotriazines is pH sensitive reaction and instead of using any acidic and basic conditions, we tried to synthesize this trimer under neutral conditions. Methods: Synthesis of 1,3,5-hexahydro symtriazine derivatives has been achieved by treating parasubstituted aniline with solution of paraformaldehyde using PEG-400 as neutral medium using grindstone method. Results: Symtriazine derivatives were synthesized in good to excellent yields (95-70%) within a short time of 5-7 minutes by grindstone technique using PEG-400 as neutral solvent medium. All the synthesized compounds were characterized by 1HNMR, 13CNMR, Mass and Melting point. Conclusion: This is the first report for the synthesis of 1,3,5-hexahydro-sym-triazine trimer starting from aniline/substituted aniline and paraformaldehyde in the presence of reusable and environmental friendly solvent media PEG-400 by grindstone technique.
Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights
Zheng, Yang,Chi, Yongjian,Bao, Ming,Qiu, Lihua,Xu, Xinfang
, p. 2129 - 2135 (2017/02/26)
A general and unprecedented gold-catalyzed tandem dual heterocyclization reaction of enynones with 1,3,5-triazines has been developed, which provides bicyclic fused furans in high to excellent yields under mild reaction conditions. In addition, mechanistic studies indicate that the reaction goes through a stepwise [3+2+2]-cycloaddition of furanyl gold intermediate, which is generated from gold-catalyzed cyclization of enynone, with two molecules of formaldimines derived in situ from 1,3,5-triazine, instead of formal [4+3]-cycloaddition.
Enantioselective Mannich Reaction Employing 1,3,5-Triaryl-1,3,5-triazinanes Catalyzed by Chiral-at-Metal Rhodium Complexes
Gong, Jun,Li, Shi-Wu,Qurban, Saira,Kang, Qiang
supporting information, p. 3584 - 3593 (2017/07/22)
Chiral-at-metal RhIII complexes catalyze the efficient enantioselective Mannich reaction of 2-acyl imidazoles with 1,3,5-triazinanes, affording the corresponding adducts in 81–99 % yield with up to >99 % enantioselectivity. This protocol performs with 0.1 mol-% of RhIII complex on gram scale without any loss in enantioselectivity.
Gold-Catalyzed Formal [4+1]/[4+3] Cycloadditions of Diazo Esters with Triazines
Zhu, Chenghao,Xu, Guangyang,Sun, Jiangtao
supporting information, p. 11867 - 11871 (2016/11/17)
Reported herein is the unprecedented gold-catalyzed formal [4+1]/[4+3] cycloadditions of diazo esters with hexahydro-1,3,4-triazines, thus providing five- and seven-membered heterocycles in moderate to high yields under mild reaction conditions. These reactions feature the use of a gold complex to accomplish the diverse annulations and the first example of the involvement of a gold metallo-enolcarbene in a cycloaddition. It is also the first utilization of stable triazines as formal dipolar adducts in the carbene-involved cycloadditions. Mechanistic investigations reveal that the triazines reacted directly, rather than as formaldimine precursors, in the reaction process.
