A novel photoisomerzation of 1,2-benzothiazine 1,1-dioxides to 1,3-benzothiazine 1,1-dioxides

被引:9
|
作者
Elghamry, Ibrahim [1 ]
Doepp, Dietrich [1 ]
Henkel, Gerald [1 ]
机构
[1] Univ Duisburg Essen, Inst Chem, D-47048 Duisburg, Germany
关键词
PIROXICAM-INDUCED PHOTOSENSITIVITY; PHOTOCHEMICAL RING-EXPANSION; PHOTOISOMERIZATION; ISOMERIZATION; DERIVATIVES; MECHANISM; SACCHARIN; ENIGMA;
D O I
10.1002/jhet.5570440416
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel facile photoconversion of 4-hydroxy-1,2-bezothiazine 1,1-dioxides (3a-e) into 4-oxo-1,3-2H-benzothiazine 1,1-dioxides (4a-e) and 4-hydroxy-2-methyl-N-(pyridin-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (PRX) into N-methyl saccharin (2) upon 254 nm irradiation in methanol or acetonitrile is reported. The structures of the products have been elucidated by spectroscopic methods and single crystal X-ray structure determination for 4a and 4d.
引用
收藏
页码:849 / 852
页数:4
相关论文
共 50 条
  • [1] Facile Preparation of Indoles and 1,2-Benzothiazine 1,1-Dioxides: Nucleophilic Addition of Sulfonamides to Bromoacetylenes and Subsequent Palladium-Catalyzed Cyclization
    Yamagishi, Masahito
    Nishigai, Ken
    Ishii, Azusa
    Hata, Takeshi
    Urabe, Hirokazu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (26) : 6471 - 6474
  • [2] N-Unsubstituted 1,2-benzothiazine 1,1-dioxides: Pd-catalyzed one-pot sonochemical access and in silico / in vitro evaluation against MtbCM
    Addu, Narender
    Miriyala, Hinuja
    Kapavarapu, Ravikumar
    Kolli, Sunder Kumar
    Pal, Manojit
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1301
  • [3] Synthesis of tetrahydrothiophene 1,1-dioxides annulated with oxazolidine ring
    Zarovnaya, I. S.
    Dul'nev, P. G.
    Pal'chikov, V. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (08) : 1199 - 1201
  • [4] Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides
    Blackburn, J.
    Molyneux, G.
    Pitard, A.
    Rice, C. R.
    Page, M. I.
    Afshinjavid, S.
    Javid, F. A.
    Coles, S. J.
    Horton, P. N.
    Hemming, K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (06) : 2134 - 2144
  • [5] Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies
    Wilkerson, Phillip D.
    Bean, Andrew C.
    Stephens, Chad E.
    HETEROCYCLIC COMMUNICATIONS, 2017, 23 (02) : 101 - 103
  • [6] Staudinger and retro-Staudinger reactions. The dichloro-β-lactam moiety as a useful handle for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides
    Fodor, Lajos
    Csomos, Peter
    Csampai, Antal
    Sohar, Pal
    TETRAHEDRON LETTERS, 2010, 51 (24) : 3205 - 3207
  • [7] Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides
    Xi, Long-Yi
    Zhang, Ruo-Yi
    Shi, Lei
    Chen, Shan-Yong
    Yu, Xiao-Qi
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 1072 - 1078
  • [8] Ring Contraction of 2,5-Dihydrobenzo[f][1,2,5]thiadiazepine 1,1-Dioxides: Access to 4H-Benzo[b][1,4]thiazine 1,1-Dioxides
    Fueloepova, Veronika
    Krchnakova, Anna
    Schuetznerova, Eva
    Zajicek, Jaroslav
    Krchnak, Viktor
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) : 1795 - 1801
  • [9] Tandem Protocol for the Synthesis of 3-Acyl Benzothiadiazine 1,1-Dioxides
    Sathe, Pratima A.
    Vadagaonkar, Kamlesh S.
    Vhatkar, Mahendra V.
    Melone, Lucio
    Chaskar, Atul C.
    CHEMISTRYSELECT, 2018, 3 (01): : 277 - 283
  • [10] Synthesis and anticancer activity of 1,2,4-Benzothiadiazine-1,1-dioxides
    Chhabra, Sumit
    Shah, Kamal
    RESULTS IN CHEMISTRY, 2023, 5