Synthesis of 1,2-benzisothiazolin-3-ones by ring transformation of 1,3-benzoxathiin-4-one 1-oxides

被引：17

作者：

Shimizu, Masao ^{[1
]}

Shimazaki, Teruaki ^{[2
]}

Yoshida, Tetsuya ^{[2
]}

Ando, Wataru ^{[1
]}

Konakahara, Takeo ^{[2
]}

机构：

[1] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan

[2] Tokyo Univ Sci, Fac Sci & Technol, Noda, Chiba 2788510, Japan

来源：

TETRAHEDRON | 2012年 / 68卷 / 21期

关键词：

Heterocycles; 1,2-Benzisothiazolin-3-one; Sulfoxide; Sulfenic acid; Hydrogen peroxide; ALPHA-SUBSTITUIERTER SULFIDE; UBER; 4-THIAISOCHROMAN-1-ONE; SULFENAMIDES; DERIVATIVES; CYCLIZATION; ACIDS;

D O I：

10.1016/j.tet.2012.03.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Benzisothiazolin-3-ones were synthesized from 1,3-benzoxathiin-4-one 1-oxides by means of a nonhazardous and inexpensive method. The 1,3-benzoxathiin-4-one 1-oxides were prepared by oxidation of 1,3-benzoxathiin-4-ones with hydrogen peroxide in the presence of a catalyst. Attack of amines on the carbonyl groups of the 1,3-benzoxathiin-4-one 1-oxides and subsequent elimination of carbonyl compounds likely produced sulfenic acids, which then underwent ring closure to afford the 1,2-benzisothiazolin-3-ones. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3932 / 3936

页数：5

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