The nitration and bromination of 2-(pentafluorosulfanyl)-1,3-benzothiazole and 2-(trifluoromethyl)-1,3-benzothiazole

被引：1
|
作者：
Guzyr, Olexandr I. [1 ]
Potikha, Lyudmila M. [1 ,2 ]
Shishkina, Svitlana V. [3 ]
Fetyukhin, Volodymyr N. [4 ]
Shermolovich, Yuriy G. [1 ]
机构：
[1] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Akad Kukharya St, UA-02660 Kiev, Ukraine
[2] Kyiv Taras Shevchenko Natl Univ, 64 Volodymyrska St, UA-01033 Kiev, Ukraine
[3] Natl Acad Sci Ukraine, State Sci Inst, Inst Single Crystals, 60 Nauky Ave, UA-61001 Kharkiv, Ukraine
[4] Life Chem Inc, 1A Dixie Ave, Niagara On The Lake, ON L0S 1J0, Canada
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2023年 / 59卷 / 4-5期
关键词：
benzothiazole; pentafluoropersulfurans; 2-(pentafluorosulfanyl)-1,3-benzothiazole; 2-(trifluoromethyl)-1,3-benzothiazole; bromination; nitration; CONTAINING CYANINE DYES; BENZOTHIAZOLES; DERIVATIVES;
D O I：
10.1007/s10593-023-03197-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The nitration and halogenation reactions of 2-(pentafluorosulfanyl)- and 2-(trifluoromethyl)-1,3-benzothiazoles were studied. Methods for the preparation of previously undescribed mononitro-substituted 1,3-benzothiazoles (4-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole, 4-nitro-2-(trifluoromethyl)-1,3-benzothiazole, and 6-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole) as well as a new method for the synthesis of the previously known 6-nitro-2-(trifluoromethyl)-1,3-benzothiazole were developed. The procedure involved the reaction of 2-(trifluoromethyl)-1,3-benzothiazole with NH4NO3 in TFAA at room temperature. An efficient method for the preparation of 2-substituted 4,5,6,7-tetrabromo-1,3-benzothiazoles based on the reaction of 2-substituted 1,3-benzothiazoles with NBS in TFA-H2SO4 at room temperature was proposed.
引用
收藏
页码：304 / 308
页数：5
相关论文
共 50 条
  • [41] 5-Chloro-2-(3,4,5-trimethoxyphenyl)-1,3-benzothiazole
    Yousuf, Sammer
    Shah, Shazia
    Ambreen, Nida
    Khan, Khalid M.
    Ahmad, Shakil
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3057 - +
  • [42] Crystal structures of hydrazones, 2-(1,3-benzothiazolyl)-NH-N=CH-Ar, prepared from arenealdehydes and 2-hydrazinyl-1,3-benzothiazole
    Nogueira, Antonio F.
    Vasconcelos, Thatyana R. A.
    Wardell, James L.
    Wardell, Solange M. S. V.
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, 2011, 226 (11): : 846 - 860
  • [43] BASE-CATALYZED REACTION OF 2-CYANOMETHYL-1,3-BENZOTHIAZOLE WITH BENZOFUROXANES
    BORAH, HN
    SANDHU, JS
    HETEROCYCLES, 1986, 24 (04) : 979 - 982
  • [44] Some Reactions of 2-Cyanomethyl-1,3-benzothiazole with Expected Biological Activity
    Hassan, A. Y.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (11) : 2856 - 2869
  • [45] A Review on Domino Condensation/Cyclization Reactions for the Synthesis of 2-Substituted 1,3-Benzothiazole Derivatives
    Liu, Xing
    Dong, Zhi-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (04) : 408 - 419
  • [46] Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
    Lungu, Lidia
    Cucicova, Caleria
    Blaja, Svetlana
    Ciocarlan, Alexandru
    Dragalin, Ion
    Barba, Alic
    Vornicu, Nicoleta
    Geana, Elisabeta-Irina
    Mangalagiu, Ionel I.
    Aricu, Aculina
    MOLECULES, 2022, 27 (16):
  • [47] Intramolecular hypervalent C=O•••S interactions in a series of 1,3-benzothiazole derivatives
    Navarrete-Vazquez, Gabriel
    Alaniz-Palacios, Alfredo
    Tlahuextl, Margarita
    Bernal-Uruchurtu, Margarita
    Tlahuext, Hugo
    CRYSTENGCOMM, 2012, 14 (04) : 1256 - 1263
  • [48] Exploring the structural landscape of 2-(thiophen-2-yl)-1,3-benzothiazole: high-Z′ packing polymorphism and cocrystallization with calix[4]tube
    Alvarenga, Meiry E.
    Valdo, Ana Karoline S. M.
    Ribeiro, Leandro
    Do Nascimento Neto, Jose Antonio
    De Araujo, Debora P.
    Da Silva, Cleiton Moreira
    De Fatima, Ngelo
    Martins, Felipe T.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2019, 75 : 667 - +
  • [49] Development of photofunctional materials using TTF derivatives containing a 1,3-benzothiazole ring
    Fujiwara, H.
    Yokota, S.
    Hayashi, S.
    Takemoto, S.
    Matsuzaka, H.
    PHYSICA B-CONDENSED MATTER, 2010, 405 (11) : S15 - S18
  • [50] 2-(2-Hydroxyphenyl)-1,3-benzothiazole-6-carbaldehyde
    Chen, Kew-Yu
    Fang, Tzu-Chien
    Chang, Ming-Jen
    Tsai, Hsing-Yang
    Luo, Ming-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2862 - +
12345