文献类型：期刊文献

英文题名：Unexpected O-H Insertion of Rhodium-Azavinylcarbenes with N-Acylhydrazones: Divergent Synthesis of 3,6-Disubstituted- and 3,5 6-Trisubstituted-1,2,4-Triazines

作者：Meng, Jiang;Wen, Min;Zhang, Shiwei;Pan, Peiwen;Yu, Xingxin[1];Deng, Wei-Ping[1]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2017

卷号：82

期号：3

起止页码：1676

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20170603327283);WOS:【SCI-EXPANDED(收录号:WOS:000394472900042)，CCR-EXPANDED(收录号:WOS:000394472900042)】；

基金：This work is supported by The National Natural Science Foundation of China (No. 21402049) and the Shanghai Comittee of Science and Technology (No. 14431902500).

语种：英文

外文关键词：Cyclization - Ketones - Reaction intermediates

摘要：A practical and efficient method for divergent synthesis of 3,6-disubstituted- and 3,S,6-trisubstituted-1,2,4-triazines via unexpected rhodium-catalyzed O-H insertion/rearrangement/conditions-controlled intramolecular cyclization and oxidation reaction under mild conditions has been developed. Notably, it is the first example for the synthesis of 1,2,4-triazines with different substituted-patterns via a common intermediate with excellent chemoselectivities by the reaction of N-acylhydrazones as aze-[3C] or [4C] synthons with N-sulfonyl-1,2,3-triazoles as aze-[2C] synthons. Furthermore, this method allows direct access to di(het)aryl ketone frameworks containing 1,2,4-triazine moiety for the first time, serving as a versatile building block for the synthesis of other useful heterocyclic skeletons, such as pyridine or pyridazinone-fused triazine in excellent yields.