Nguyen Thi Mo, Cao Hoang Anh, Thuong Cao Thi Thuong, Koyama Satoki, Mac Dinh Hung, Nguyen Thanh Binh
Faculty of Chemistry, VNU University of Science, Vietnam National University in Hanoi, 19 Le Thanh Tong, Hanoi, Viet Nam.
Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashihiroshima, Hiroshima 739-8526, Japan.
J Org Chem. 2020 Oct 2;85(19):12058-12066. doi: 10.1021/acs.joc.0c00918. Epub 2020 Sep 15.
[2,1]Benzothiazine ,-dioxides were synthesized by simply heating -nitrostyrenes with elemental sulfur in 3-picoline with complete atom economy. This reaction was found to occur without any added catalyst and consist of a cascade of reduction of the nitro group, sulfuration of a C-H of the double bond, oxidation of a sulfur atom to its highest oxidation state by the migration of two oxygen atoms from the nitro group, and formation of new N-S bonds. Furthermore, the method could also be applied to -nitrocinnamamides and cinnamate esters.
通过在3-甲基吡啶中简单地将对硝基苯乙烯与元素硫加热，以完全原子经济性合成了[2,1]苯并噻嗪二氧化物。发现该反应无需添加任何催化剂即可发生，并且包括硝基的一系列还原、双键的C-H硫化、通过两个氧原子从硝基迁移将硫原子氧化到其最高氧化态以及形成新的N-S键。此外，该方法也可应用于对硝基肉桂酰胺和肉桂酸酯。
