An efficient route to 3-trifluoromethylpyrazole via cyclization/1,5-H shift and its applications in the synthesis of bioactive compounds

被引：29
|
作者：
Wang, Yongdong [1 ]
Han, Jing [2 ]
Chen, Jie [2 ]
Cao, Weiguo [1 ,2 ,3 ,4 ]
机构：
[1] Shanghai Univ, Sch Environm & Chem Engn, Shanghai 200444, Peoples R China
[2] Shanghai Univ, Dept Chem, Innovat Drug Res Ctr, Shanghai 200444, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2015年 / 71卷 / 43期
基金：
中国国家自然科学基金;
关键词：
Trifluoromethyl; Pyrazole; 1,5-H shift; Cyclization; KETONES; REGIOSELECTIVITY; FLUORINE;
D O I：
10.1016/j.tet.2015.09.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A methodology for regioselective synthesis of 3-trifluoromethylpyrazole from the reaction of trifluoromethyl alkenone and tosylhydrazone has been developed. The reaction was proposed to proceed through a tandem cyclization and 1,5-H shift reaction, which can be applied to the synthesis of bioactive compounds like Celecoxib, Mavacoxib, and SC-560. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8256 / 8262
页数：7
相关论文
共 50 条
  • [1] RADICAL CYCLIZATION OF EPOXYKETONES VIA A 1,5BU(N)3SN GROUP OR A 1,5-H ATOM TRANSFER
    KIM, S
    KOH, JS
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (18) : 1377 - 1378
  • [2] Rh(II)-catalysed N2-selective arylation of benzotriazoles and indazoles using quinoid carbenes via 1,5-H shift
    Sarkar, Souradip
    Bhunya, Sourav
    Pan, Subarna
    Datta, Arnadeep
    Roy, Lisa
    Samanta, Rajarshi
    CHEMICAL COMMUNICATIONS, 2024, 60 (35) : 4727 - 4730
  • [3] C-H Bond Functionalization via [1,5]-Hydride Shift/Cyclization Sequence: Approach to Spiroindolenines
    Wang, Peng-Fei
    Jiang, Chun-Huan
    Wen, Xiaoan
    Xu, Qing-Long
    Sun, Hongbin
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02): : 1155 - 1162
  • [4] A facile and rapid route for the synthesis of novel 1,5-substituted tetrazole hydantoins and thiohydantoins via a TMSN3-Ugi/RNCX cyclization
    Medda, Federico
    Hulme, Christopher
    TETRAHEDRON LETTERS, 2012, 53 (42) : 5593 - 5596
  • [5] A STUDY OF PERISELECTIVITY IN THE THERMAL CYCLIZATION REACTIONS OF DIENE-CONJUGATED DIAZO-COMPOUNDS - 1,7-CYCLIZATION AS A ROUTE TO 3H-1,2-DIAZEPINES AND 1,5-CYCLIZATION LEADING TO NEW REARRANGEMENT REACTIONS OF 3H-PYRAZOLES
    ROBERTSON, IR
    SHARP, JT
    TETRAHEDRON, 1984, 40 (16) : 3095 - 3112
  • [6] Synthesis of triptoquinone H and its C-5 epimer via efficient asymmetric dearomative cyclization
    Cao, Zhen
    Du, Kang
    Liu, Jianhui
    Tang, Wenjun
    TETRAHEDRON, 2016, 72 (14) : 1782 - 1786
  • [7] Synthesis of Ring-Fused 1-Benzazepines via [1,5]-Hydride Shift/7-Endo Cyclization Sequences
    Suh, Chang Won
    Kwon, Su Jin
    Kim, Dae Young
    ORGANIC LETTERS, 2017, 19 (06) : 1334 - 1337
  • [8] Shifting the Reactivity of Bis-propargyl Ethers from Garratt-Braverman Cyclization Mode to 1,5-H Shift Pathway To Yield 3,4-Disubstituted Furans: A Combined Experimental and Computational Study
    Das, Joyee
    Das, Eshani
    Jana, Saibal
    Addy, Partha Sarathi
    Anoop, Anakuthil
    Basak, Amit
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (02): : 450 - 457
  • [9] Synthesis of 1,5-benzothiazepnes and 1,5-benzooxazepines via cyclization of trans-3-benzylidenechroman-4-ones and 2-aminothiophenols.
    Biehl, ER
    Zhang, HM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U215 - U215
  • [10] Construction of Optically Active 2H- and 3H-Pyrroles by Cyclization and Chirality Maintaining 1,5-Ester Shift Reactions
    Li, Dan
    Wang, Linqing
    Yang, Yuling
    Zhang, Minmin
    Peng, Tianyu
    Yang, Dongxu
    Wang, Rui
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (16) : 3744 - 3750
12345