Synthesis of 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones with the aid of samarium(II) iodide

被引:14
|
作者
Zhong, WH
Zhang, YM
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
[2] Chinese Acad Sci, Organomet Chem Lab, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
samarium(II) iodide; nitro group; disulfide; diselenide; reductive cyclization; 2H-1,4-benzothiazin-3(4H)-one; 2H-1,4-benzoselenazin-3(4H)-one;
D O I
10.1016/S0040-4039(01)00360-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bis(o-nitrophenyl) disulfides or diselenides were easy to reduce by samarium(II) iodide to produce the active intermediates 2 in situ, which readily react with alpha -halocarboxylic derivatives to yield the corresponding products 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields under mild conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3125 / 3127
页数:3
相关论文
共 50 条
  • [1] Facile synthesis of 2H-1,4-benzothiazin-3(4H)-ketoximes and 2H-1,4-benzoselenazin-3(4H)-ketoximes promoted by SmI2
    Xu, XL
    Zhang, YM
    [J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (20) : 3537 - 3543
  • [2] The inhibition of monoamine oxidase by 2H-1,4-benzothiazin-3(4H)-ones
    Hitge, Rialette
    Petzer, Jacobus P.
    Petzer, Anel
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2022, 77
  • [3] Synthesis and structure of 2-(nitromethylene)-2H-1,4-benzothiazin-3(4H)-one
    V. M. Berestovitskaya
    V. A. Tafeenko
    S. V. Makarenko
    K. D. Sadikov
    I. V. Chernyshev
    [J]. Russian Journal of General Chemistry, 2006, 76 : 135 - 140
  • [4] Synthesis and structure of 2-(nitromethylene)-2H-1,4-benzothiazin-3(4H)-one
    Berestovitskaya, VM
    Tafeenko, VA
    Makarenko, SV
    Sadikov, KD
    Chernyshev, IV
    [J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2006, 76 (01) : 135 - 140
  • [5] 2-(4-Chlorobenzoylmethyl)-2H-1,4-benzothiazin-3(4H)-one
    Zhang, Ping
    Du, Na
    Wang, Lan-Zhi
    Li, Yuan
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O746 - U1722
  • [6] 4-(Prop-2-ynyl)-2H-1,4-benzothiazin-3(4H)-one
    Sebbar, Nada Kheira
    Zerzouf, Abdelfettah
    Essass, El Mokhtar
    Saadi, Mohamed
    El Ammari, Lahcen
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O641 - +
  • [7] Novel syntheses of 2,3-dihydro-1,5-benzothiazepin-4 (5H)-ones and 2H-1,4-benzothiazin-3(4H)-ones
    Katritzky, AR
    Odens, HH
    Zhang, SM
    Rostek, CJ
    Maender, OW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20): : 6792 - 6796
  • [8] A GENERAL AND CONVENIENT SYNTHESIS OF 2H-1,4-BENZOXAZIN-3(4H)-ONES
    SHRIDHAR, DR
    JOGIBHUKTA, M
    KRISHNAN, VSH
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1982, 14 (03) : 195 - 197
  • [9] AN IMPROVED ALKYLATION OF 2H-1,4-BENZOTHIAZIN-3(4H)-ONE AND RELATED HETEROCYCLIC ANILIDES
    MARFAT, A
    CARTA, MP
    [J]. SYNTHESIS-STUTTGART, 1987, (05): : 515 - 517
  • [10] 4-(1H-Benzimidazol-2-ylmethyl)-2H-1,4-benzothiazin-3(4H)-one
    Fun, Hoong-Kun
    Rosli, Mohd Mustaqim
    Gowda, Janardhana
    Khader, A. M. A.
    Kalluraya, B.
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1495 - U2133