866124-84-7Relevant academic research and scientific papers
Synthesis and reactions of 3-alkylsulfanyl-1,3-dihydro-2,1-benzisothiazole 2,2-dioxides
Modrzejewska, Helena,Wojciechowski, Krzysztof
, p. 8848 - 8854 (2005)
Alkyl- and arylsulfanylation of 1,3-dihydro-2,1-benzisothiazole 2,2-dioxides (benzosultams) 1a-c and pyridosultam 1d with dialkyl and diaryl disulfides provides dithioacetals of 2-aminobenzaldehydes 6-13. 1,3-Dimethylbenzosultam 19 with disulfides forms 3-alkyl(aryl)sulfanyl-1,3- dimethylbenzosultams 20-22 that undergo thermal extrusion of SO2 followed by a [1,5] sigmatropic hydrogen shift in the intermediate aza-ortho-xylylene leading to 1-arylvinyl sulfides 24-26. Tandem alkylation-sulfanylation of benzo- and pyridosultams 1a-d with 4-bromobutyl thiocyanate gives tetrahydrothiopyrano-spiro-benzosultams 27-30 that, after extrusion of SO2 and [1,5] hydrogen shift, form 2-aryl-5,6-dihydro- 4H-thiopyrans 32-35. Alkylation of pyridosultam 1d with 3-chloropropyl thiocyanate leads directly to 2-pyrido-3,4-dihydrothiophene derivative 37.
