Fused pyrazole synthesis by N-N bond formation: The pyrazolo[5,1-b]benzothiazole system

被引：0
|
作者：
Bates, DK
Kohrt, JT
Folk, H
Xia, MD
机构：
来源：
HETEROCYCLIC COMMUNICATIONS | 1997年 / 3卷 / 03期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of (benzothiazol-2-yl)acetone oxime 1 with excess trifluoroacetic anhydride (TFAA) at room temperature produces 2-methyl-3-trifluoroacetylpyrazoIo[5,1-b]benzothiazole 11 in 71-92 % yield depending on the purity of the oxime. Compound II is reduced by NaBH4 to the corresponding alcohol 12 and hydrolyzed to the corresponding carboxylic acid 13 under alkaline conditions. Other reagents commonly used to promote Beckmann rearrangement of oximes cause only decomposition of 1 to intractable materials.
引用
收藏
页码：201 / 206
页数：6
相关论文
共 50 条
  • [21] Synthesis of the first example of the imidazo-[5,1-b]oxazole heteroaromatic system
    E. V. Aleksandrova
    N. M. Kochergin
    Chemistry of Heterocyclic Compounds, 2007, 43 (5) : 669 - 670
  • [22] Mechanism of pyrazole formation in [13C-2] labeled glycine model systems:: N-N bond formation during Maillard reaction
    Yaylayan, VA
    Haffenden, LJW
    FOOD RESEARCH INTERNATIONAL, 2003, 36 (06) : 571 - 577
  • [23] Domino synthesis of fused pyrazolo[5,1-b]quinazolin-9(1H)-ones catalyzed by CuI via subsequent Michael addition and elimination
    Zhang, Yan
    Xu, Jing
    Li, Chao
    Wang, Xiang-Shan
    TETRAHEDRON, 2015, 71 (46) : 8732 - 8737
  • [24] Copper-catalyzed oxidative dehydrogenative N-N bond formation for the synthesis of N,N′-diarylindazol-3-ones
    Dai, Guo
    Yang, Luo
    Zhou, Wang
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 229 - 231
  • [25] Multicomponent Pyrazole Synthesis from Alkynes, Nitriles, and Titanium Imido Complexes via Oxidatively Induced N-N Bond Coupling
    Pearce, Adam J.
    Harkins, Robin P.
    Reiner, Benjamin R.
    Wotal, Alexander C.
    Dunscomb, Rachel J.
    Tonks, Ian A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (09) : 4390 - 4399
  • [26] N-N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts
    Tota, Arianna
    Colella, Marco
    Carlucci, Claudia
    Aramini, Andrea
    Clarkson, Guy
    Degennaro, Leonardo
    Bull, James A.
    Luisi, Renzo
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (01) : 194 - 199
  • [27] Efficient Synthesis of Pyrazoles: Oxidative C-C/N-N Bond-Formation Cascade
    Neumann, Julia J.
    Suri, Mamta
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (42) : 7790 - 7794
  • [28] Synthesis, Characterization, and Biological Evaluation of Some Novel Pyrazolo[5,1-b]thiazole Derivatives as Potential Antimicrobial and Anticancer Agents
    Alsayari, Abdulrhman
    Bin Muhsinah, Abdullatif
    Asiri, Yahya, I
    Al-aizari, Faiz A.
    Kheder, Nabila A.
    Almarhoon, Zainab M.
    Ghabbour, Hazem A.
    Mabkhot, Yahia N.
    MOLECULES, 2021, 26 (17):
  • [29] Intramolecular Metal-Free N-N Bond Formation with Heteroaromatic Amines: Mild Access to Fused-Triazapentalene Derivatives
    Daniel, Matthieu
    Hiebel, Marie-Aude
    Guillaumet, Gerald
    Pasquinet, Eric
    Suzenet, Franck
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (07) : 1525 - 1529
  • [30] TRICARBONYLMETHANE ACYLHYDRAZONES - REACTIONS UNDER ACYLATING CONDITIONS AND FORMATION OF FUSED ISOXAZOLE DERIVATIVES WITH CONCOMITANT N-N BOND-CLEAVAGE
    SOMOGYI, L
    SOHAR, P
    LIEBIGS ANNALEN-RECUEIL, 1995, (10): : 1903 - 1906
12345