2,1‐Benzisothiazoline 2,2‐dioxide and derivatives

Abstract

Synthesis of new 2,1‐benzisothiazoline 2,2‐dioxides 1 and some of its benzene ring substitution derivatives was accomplished by two different methods of cyclisation. Also a number of new N‐substituted derivatives, obtained by treatment of 1 and analogues with aliphatic and aromatic acid chlorides are described.

An Aminative Rearrangement of O‐(Arenesulfonyl)hydroxylamines: Facile Access to ortho‐Sulfonyl Anilines

“…The resulting 6‐bromosultam 9 has not been reported in the literature, in contrast to the 5‐isomer which has been used in a number of medicinal chemistry campaigns (inset box) [17] . The 5‐isomer can be readily obtained through electrophilic bromination and seems likely that poor synthetic accessibility has prevented the 6‐isomer from being explored [18] . Finally, to further stress the practical utility of our method, we compare synthetic access to all four methylated regioisomers of 2‐aminobenzenesulfonic acid using our approach versus aniline sulfonation (Figure 2C).…”

“…[17] The 5-isomer can be readily obtained through electrophilic bromination and seems likely that poor synthetic accessibility has prevented the 6-isomer from being explored. [18] Finally, to further stress the practical utility of our method, we compare synthetic access to all four methylated regioisomers of 2-amino-Scheme 2. [a] Yields are isolated.…”

Sulfonilamidometilación intramolecular de 2-naftilmetan y 2-(2-naftil)etansulfonamidas

“…Este tipo de reacción de SNA intramolecular ha sido utilizado en varios casos para la síntesis de estas γ-benzosultamas. (143)(144) En 1986, Chiarino y Contri (145) sintetizaron estas sultamas a partir de la ciclización de 2-clorobencilsulfonamidas (119) o 2-aminobencilsulfonatos de sodio (120). Para el primer caso se calentó a reflujo una mezcla de la sulfonamida con carbonato de potasio y polvo de cobre-bronce en 2,3-dimetilanilina como solvente durante 3 h. En el segundo caso, la ciclización se produjo calentando el sulfonato con oxicloruro de fósforo a reflujo.…”