78386-71-7Relevant articles and documents
I2/K2S2O8 Mediated Direct Oxidative Annulation of Alkylazaarenes with Amidines for the Synthesis of Substituted 1,3,5-Triazines
Zhang, Jun,Zheng, Tingting,Zhang, Jidong
supporting information, p. 860 - 865 (2020/02/20)
A direct method for the synthesis of heteroaryl-substituted 1,3,5-triazines from readily available methyl-azaarenes and amidines has been developed. The present method involves iodine mediated cascade aerobic C(sp3)–H oxidative amination and following condensation, cyclization with amidine. Both of methyl quinoline, pyridine and benzothiazole derivatives could be well tolerated to react with various amidines leading to corresponding products in good to excellent yields.
IEDDA Reaction of the Molecular Iodine-Catalyzed Synthesis of 1,3,5-Triazines via Functionalization of the sp3 C-H Bond of Acetophenones with Amidines: An Experimental Investigation and DFT Study
Tiwari, Abhishek R.,Nath, Shilpa R.,Joshi, Kaustubh A.,Bhanage, Bhalchandra M.
, p. 13239 - 13249 (2017/12/26)
The present work reports an inverse electron demand Diels-Alder (iEDDA)-type reaction to synthesize 1,3,5-trizines from acetophenones and amidines. The use of molecular iodine in a catalytic amount facilitates the functionalization of the sp3 C-H bond of acetophenones. This is a simple and efficient methodology for the synthesis of 1,3,5-triazines in good to excellent yields under transition-metal-free and peroxide-free conditions. The reaction is believed to take place via an in situ iodination-based oxidative elimination of formaldehyde. DFT calculations at the M062X/6-31+G(d,p) level were employed to investigate the reaction mechanism. Reaction barriers for the cycloaddition as well as a formaldehyde expulsion steps were computed, and a multistep mechanism starting with the nucleophilic attack by benzamidine on an in situ generated imine intermediate has been proposed. Both local and global reactivity descriptors were used to study the regioselectivity of the addition steps.
Iridium-catalyzed cascade dehydrogenation, ring-closure reaction leading to 2,4,6-triaryl-1,3,5-triazines
Shi, Gang,He, Fei,Che, Youxin,Ni, Caihua,Li, Ying
, p. 380 - 386 (2016/04/20)
An efficient iridium-catalyzed dehydrogenation, ring-closure reaction, has been developed via a cascade sequence, in which [Cp?IrI2]2/Xantphos proved to be the most efficient catalyst for the synthesis of 2,4,6-triaryl-1,3,5-triazines from stable aryl-substituted alcohols and amidines. It was the first case of iridium catalyst successful application in such transformation.