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
相关论文
共 50 条
  • [21] One-pot mild and efficient synthesis of [1,3]thiazino[3,2-a]indol-4-ones and their anti-proliferative activity
    Rhodes, Steven
    Short, Spencer
    Sharma, Sidhika
    Kaur, Ramneet
    Jha, Mukund
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (16) : 3914 - 3920
  • [22] Skeletal editing of benzodithiol-3-ones for the assembly of benzo[d][1,3]oxathiin-4-ones
    Lv, Wenxin
    Kong, Xuan
    Qing, Yushang
    Zheng, Jing
    Yin, Yuan
    Zhou, Yao
    Wang, Dunjia
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (18): : 4979 - 4985
  • [23] RETRACTED: One-Pot Synthesis of [1,2]Isoxazolidin-5-ones and [1,2]Oxazin-6-ones (Retracted Article)
    Arfaoui, Aicha
    Beltaief, Imen
    Amri, Hassen
    SYNTHETIC COMMUNICATIONS, 2011, 41 (10) : 1536 - 1543
  • [24] Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents
    Subhedar, Dnyaneshwar D.
    Shaikh, Mubarak H.
    Arkile, Manisha A.
    Yeware, Amar
    Sarkar, Dhiman
    Shingate, Bapurao B.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (07) : 1704 - 1708
  • [25] Facile Synthesis of Novel Pyrimido[1,2-a]pyrimidin-4-ones from Highly Reactive Malonates
    Gullu, Mustafa
    Dincsonmez, Ali
    Ozyavas, Oznur
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (11) : 2113 - 2120
  • [26] Synthesis of Spiro[imidazole-4,3′-pyrrolo[1,2-a]quinolin]-5-ones via 1,3-Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol-4-ones
    Molchanova, Marina V.
    Ikonnikova, Viktoria A.
    Smirnov, Alexander Yu.
    Solyev, Pavel N.
    Baranov, Mikhail S.
    Mikhaylov, Andrey A.
    CHEMISTRYSELECT, 2024, 9 (08):
  • [27] Chemodivergent Synthesis of Benzothiadiazin-3-one 1-Oxides and Benzisothiazol-3-ones via Visible Light-Promoted Intramolecular N-S Bond Formation
    Li, Huimin
    Xiong, Zhiqiang
    Sheng, Shouri
    Chen, Junmin
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24) : 16949 - 16959
  • [28] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW 1,3-THIAZOLYLQUINAZOLIN-4-(3H)-ONES
    Patel, N. B.
    Patel, J. N.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 18 (03) : 247 - 250
  • [29] Ionic liquid promoted one pot approach for the synthesis of pyrido[1,2-c][1,3,5] thiadiazin-4-ones and thiazolo[3,2-c][1,3,5]thiadiazin-4-ones in water
    Siddiqui, I. R.
    Srivastava, Arjita
    Srivastava, Anjali
    Shamim, Shayna
    Shireen
    Waseem, Malik Abdul
    ARABIAN JOURNAL OF CHEMISTRY, 2018, 11 (02) : 256 - 264
  • [30] Synthesis of Highly Substituted 1,2-Diazetidin-3-ones, Small-Ring Scaffolds for Drug Discovery
    Santos, Marilia S.
    Nortcliffe, Andrew
    Lewis, William
    Bradshaw, Tracey D.
    Moody, Christopher J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (33) : 8325 - +
12345