Synthesis and reactions of 3-alkylsulfanyl-1,3-DIHYDRO-2,1-BENZISOTHIAZOLE 2,2-DIOXIDE (cas 111248-89-6)s

Add time:08/29/2019    Source:sciencedirect.com

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.

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