Facile Synthesis of Novel N-Aryl-4,5,6,7-tetrahydro-benzosultams by Oxyfunctionalisation of Bicyclic Isothiazolium Salts*

Abstract

Abstract3-Hydroxy- (17a - j) and 3-alkoxy-4,5,6,7-tetrahydro-benzosultams 18a-m were prepared in good yields by oxidation of the bicyclic isothiazolium salts 10 with magnesium monoperoxyphthalate (MMPP·6H2O) in acetonitrile or corresponding alcohol. A HPLC-API-MS(MS) method was used to monitor the oxidation process of 10 with MMPP. 3-Oxo-4,5,6,7-tetrahydro-benzosultams 19a - c, h, j were also obtained.

Crystal structure of rac-cis-N-(2,4-dinitrophenyl)-3,4-diphenyl-5H-1,2-oxathiol- 5-amine 2-oxide, C21H15N3O6S, sultim and sultam structures – part 4

“…The oxidation of monocyclic and bicyclic isothiazolium salts has been research intensively since the last years [1][2][3][4][5][6][7] and can be classified in two principle oxidation methods. Atfirst, the salts can be oxidized with H 2 O 2 in acetic acid to yield 3-hydroperoxysultims rac-cis/ trans,s ultams and 3-oxosultams [1][2][3][4][5].…”

“…Atfirst, the salts can be oxidized with H 2 O 2 in acetic acid to yield 3-hydroperoxysultims rac-cis/ trans,s ultams and 3-oxosultams [1][2][3][4][5]. Furthermore, the isothiazolium salts reacted with magnesium monoperoxyphthalate (MMPP)inwater or alcohol to obtain the 3-hydroxysultims rac-cis/ trans,sultams or 3-alkoxysultams [6,7]. The rac-cis-N -(2,4-dinitrophenyl)-3,4-diphenyl-5H -1,2-oxathiol-5-amine 2-oxidew as obtained unexpectedly after oxidation of the isothiazolium salt to 3-hydroxysultim, ring cleavage between the sulfura nd nitrogen atoms, rearrangement and cyclization.…”