Synthesis of 1-methyl-7-(trifluoromethyl)-1<i>H</i>-pyrido[2,3-<i>c</i>][1,2]thiazin-4(3<i>H</i>)-one 2,2-dioxide
作者:Frank T. Coppo、Maged M. Fawzi
DOI:10.1002/jhet.5570350302
日期:1998.5
isocyanate, phenyl isocyanate and 2,4-dichloro-5-(2-propynyloxy)phenyl isothiocyanate gave, respectively, 4-[(2,4-dichlorophenyl)methoxy]-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazine 2,2-dioxide (5), methyl 2-[[1-methyl-2,2-dioxido-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4-yl]oxy]propanoate (6), 1,3,3-trimethyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide
2-溴-6-(三氟甲基)-3-吡啶甲酸甲酯(1)与甲磺酰胺的反应得到2-[((甲基磺酰基)氨基] -6-(三氟甲基)-3-吡啶甲酸甲酯(2)。化合物的烷基化2用甲基碘,然后将所得2- [甲基(甲磺酰基)氨基] -6-(三氟甲基)环化-3-吡啶羧酸甲酯(3),得到1-甲基-7-(三氟甲基)-1 ħ -吡啶并[2,3-c] [1,2]噻嗪-4(3 H)-一个2,2-二氧化物(4)。化合物4的反应与α,2,4-三氯甲苯,溴丙酸甲酯,碘甲烷,3-三氟甲基苯基异氰酸酯,苯基异氰酸酯和2,4-二氯-5-(2-丙炔氧基)苯基异硫氰酸酯分别得到4-[((2,4-二氯苯基)甲氧基] -1-甲基-7-(三氟甲基)-1 H-吡啶并[2,3- c ] [1,2]噻嗪2,2-二氧化物(5),甲基2-[[1-甲基- 2,2-二氧化物-7-(三氟甲基)-1 H-吡啶并[2,3- c ] [1,2]噻嗪-4-基]氧基]丙酸酯(6),1