Bakulev Vasiliy A, Berseneva Vera S, Belskaia Natalia P, Morzherin Yury Yu, Zaitsev Andreiy, Dehaen Wim, Luyten Ingrid, Toppet Suzanne
Department of Technology and Organic Synthesis, Urals State Technical University, 620002, Ekaterinburg, Russia.
Org Biomol Chem. 2003 Jan 7;1(1):134-9. doi: 10.1039/b207854f.
A systematic study of the reactions of dimethyl acetylenedicarboxylate (DMAD) and methyl propynoate with 5-mercaptoazoles and pyridine-2-thiones has been carried out and as a result, a number of novel imidazo[1,5-b]thiazin-4-ones 6a,b, pyrazolo[1,5-b] thiazin-4-ones 15a-f, imidazo[1,5-b]thiazol-4-ones 7a,b and thiazolo[3,2-a]pyridines 21a-c have been prepared. The influence of the size of the ring of the starting "cyclic" thioamides on the size of the fused ring in the reaction products has been established. The preferred formation of a six-membered thiazine ring took place in the reactions of 5-mercaptoazoles. In contrast, the five membered thiazolidine ring is formed in reactions of pyridine-2-thiones. In both cases the product is a five-membered ring fused to a six-membered heterocycle.
对乙炔二甲酸二甲酯（DMAD）和丙酸甲酯与5-巯基唑和2-吡啶硫酮的反应进行了系统研究，结果制备了一系列新型咪唑并[1,5-b]噻嗪-4-酮6a,b、吡唑并[1,5-b]噻嗪-4-酮15a-f、咪唑并[1,5-b]噻唑-4-酮7a,b和噻唑并[3,2-a]吡啶21a-c。已确定起始“环状”硫代酰胺的环大小对反应产物中稠合环大小的影响。在5-巯基唑的反应中优先形成六元噻嗪环。相反，在2-吡啶硫酮的反应中形成五元噻唑烷环。在这两种情况下，产物都是与六元杂环稠合的五元环。
