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
收藏
页码：3932 / 3936
页数：5
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