Iodobenzene-catalyzed preparation of 3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxides from 2-Aryl-N-methoxyethanesulfonamides with m-chloroperoxybenzoic acid

被引：44
|
作者：
Moroda, Atsushi [1 ]
Togo, Hideo [1 ]
机构：
[1] Chiba Univ, Grad Sch Sci, Chiba 2638522, Japan
来源：
SYNTHESIS-STUTTGART | 2008年 / 08期
关键词：
iodobenzene; catalysis; cyclizations; hypervalent iodine; sulfonamides;
D O I：
10.1055/s-2008-1042945
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Iodobenzene-catalyzed cyclization of 2-aryl-N-methoxyethanesulfonamides with m-chloroperoxybenzoic acid results in the corresponding 1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxides in moderate to good yields. In this reaction, reactive hypervalent iodine [(hydroxy)(tosyloxy)iodo] benzene, formed in situ, reacts with the 2 -aryl-N-methoxyethanesulfonamides in an electrophilic manner at the aromatic ring to give the corresponding 1-methoxy-3,4-dihydro-1H-2, 1-benzothiazine 2,2-dioxides.
引用
收藏
页码：1257 / 1261
页数：5
相关论文
共 50 条
  • [1] Heteropolyacid as an efficient catalyst for synthesis of 3,4-dihydro-1H-2,3-benzothiazine 2,2-dioxides
    Canepa, Alicia S.
    Sasiambarrena, Leandro D.
    Bravo, Rodolfo D.
    SYNTHETIC COMMUNICATIONS, 2008, 38 (15) : 2655 - 2661
  • [2] NOVEL SYNTHESIS OF 3,4-DIHYDRO-1H-2,1,3-BENZOTHIADIAZINE 2,2-DIOXIDES
    PEWS, RG
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12): : 2032 - 2034
  • [3] An efficient synthesis of 3,4-dihydro-1H-2,3-benzothiazine 2,2-dioxides using amberlyst 15 and Amberlyst XN 1010
    Bravo, RD
    Cánepa, AS
    SYNTHETIC COMMUNICATIONS, 2002, 32 (23) : 3675 - 3680
  • [4] MASS-SPECTRA OF HETEROCYCLIC-COMPOUNDS .6. 3,4-DIHYDRO-1H-2,3-BENZOTHIAZINE 2,2-DIOXIDES
    ZINCZUK, J
    BRAVO, RD
    ORAZI, OO
    CORRAL, RA
    ORGANIC MASS SPECTROMETRY, 1990, 25 (10): : 517 - 521
  • [5] Facile Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxides and Related Reaction with 1,3-Diiodo-5,5-dimethylhydantoin under Photochemical Conditions
    Moroda, Atsush
    Furuyama, Shusuke
    Togo, Hideo
    SYNLETT, 2009, (08) : 1336 - 1340
  • [6] A straightforward synthesis of 4-substituted 3,4-dihydro-1H-2, 1, 3-benzothiadiazine 2,2-dioxides
    Agejas, J
    García-Navío, JL
    Lamas, C
    TETRAHEDRON LETTERS, 2000, 41 (50) : 9819 - 9823
  • [7] Preparation of 3,4-dihydro-2,1-benzothiazine 2,2-dioxide skeleton from N-methyl 2-(aryl)ethanesulfonamides with (diacetoxyiodo)arenes
    Togo, H
    Harada, Y
    Yokoyama, M
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03): : 926 - 929
  • [8] Enantioselective synthesis of C3-functionalized 2,1-benzothiazine 2,2-dioxides by N-heterocyclic carbene catalysis
    Mroczynska, Karina
    Dobrzanska, Liliana
    Rafinski, Zbigniew
    CHEMICAL COMMUNICATIONS, 2024, 60 (56) : 7176 - 7179
  • [9] Facile Synthesis of 4-Substituted 3,4-Dihydro-1H-2,1,3-Benzothiadiazine 2,2-Dioxides
    Lee, Chai-Ho
    Jin, Guo Fan
    Lim, Hyun Wha
    Yang, Eun Hye
    Lee, Jong-Dae
    Nakamura, Hiroyuki
    Ban, Hyun Seung
    Kang, Sang Ook
    HETEROATOM CHEMISTRY, 2011, 22 (02) : 192 - 197
  • [10] 2,1-Benzothiazine 2,2-Dioxides. 8*. Synthesis and Structure of 2'-Amino-2-Oxo-1,2-Dihydro-6'H-Spiro-[Indole-3,4'-Pyrano[3,2-c][2,1]Benzothiazine]-3'-Carbonitrile 5',5'-Dioxides
    I. V. Ukrainets
    L. A. Petrushova
    N. L. Bereznyakova
    Liu Yangyang
    Chemistry of Heterocyclic Compounds, 2014, 50 : 1346 - 1353
12345