Regiospecific preparation of 1,4,5-trisubstituted pyrazoles from 2-(1H-1,2,3-benzotriazol-1-yl)-3-(4-aryl)-2-propenals

被引：15
|
作者：
Katritzky, Alan R. [1 ]
Vakulenko, Anatoliy V. [1 ]
Akue-Gedu, Rufine [1 ]
Gromova, Anna V. [1 ]
Witek, Rachel [1 ]
Rogers, James W. [1 ]
机构：
[1] Univ Florida, Dept Chem, Ctr Heterocycl Compounds, Gainesville, FL 32611 USA
来源：
ARKIVOC | 2007年
关键词：
pyrazoles; regiospecific synthesis; cyclization reaction;
D O I：
10.3998/ark.5550190.0008.102
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of alpha-benzotriazolyl-alpha,beta-unsaturated aldehydes with monosubstituted hydrazines followed by alkylation at the 4- position of the pyrazoline ring and elimination of the benzotriazole group affords 1,4,5- trisubstituted pyrazoles in overall yields of 52 - 79%.
引用
收藏
页码：9 / 21
页数：13
相关论文
共 50 条
  • [1] Microwave assisted synthesis and antimicrobial activity of novel 1-[1/2-(1-Benzyl-1H-[1,2,3] triazol-4-ylmethoxy)-naphthalen-2/1-yl]-3-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-propenones
    Ashok, Dongamanti
    Ganesh, Arram
    Lakshmi, Bommidi Vijaya
    Ravi, Sidda
    Ramesh, Banoth
    ORGANIC COMMUNICATIONS, 2015, 8 (02) : 24 - 35
  • [2] A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles
    Thomas, Joice
    John, Jubi
    Parekh, Nikita
    Dehaen, Wim
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10155 - 10159
  • [3] Synthesis of 3,4,5-Trisubstituted 1H-Pyrazoles Based on 2,3-Dienoates with a Pyrrolidinedione Fragment
    G. M. Gindullina
    I. M. Sakhautdinov
    Russian Journal of Organic Chemistry, 2025, 61 (1) : 49 - 53
  • [4] Organocatalytic 1,3-Dipolar Cycloaddition Reaction of β-Keto Amides with Azides - Direct Access to 1,4,5-Trisubstituted 1,2,3-Triazole-4-carboxamides
    Zhou, Xiao
    Xu, Xianhong
    Liu, Kun
    Gao, Hua
    Wang, Wei
    Li, Wenjun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (10) : 1886 - 1890
  • [5] Three-Component Coupling of α-Trifluoromethyl Carbonyls, Azides and Amines for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles
    Gao, Ge
    Kuantao
    Mao
    Lv, Leiyang
    Li, Zhiping
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (08) : 1402 - 1408
  • [6] SYNTHESIS OF 3,5-DIARYL-4-(1H-IMIDAZOL-2-YL)-1H-PYRAZOLES FROM 2-PHENACYL-1H-IMIDAZOLE
    Dzvinchuk, I. B.
    Nesterenko, A. M.
    Lozinskii, M. O.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (01) : 66 - 71
  • [7] Enamine-Mediated 1,3-Dipolar Cycloaddition Reaction of Curcumin Derivatives with Azides: Direct Access to 1,4,5-Trisubstituted 1,2,3-Triazoles
    Shi, Zhenyan
    Li, Wenjun
    SYNTHESIS-STUTTGART, 2017, 49 (09): : 2081 - 2087
  • [8] Synthesis of some new 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the Vilsmeier-Haack reaction -: Isolation of the key intermediate 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles
    Kumar, A
    Prakash, O
    Kinger, M
    Singh, SP
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2006, 84 (03): : 438 - 442
  • [9] Synthesis of 1H-1,2,3-triazole-4-carbonitriles as building blocks for promising 2-(triazol-4-yl)-thieno[2,3-d]pyrimidine drug candidates
    Sekh, Taras, V
    Shyyka, Olga Y.
    Pokhodylo, Nazariy T.
    Obushak, Mykola D.
    SYNTHETIC COMMUNICATIONS, 2021, 51 (20) : 3175 - 3186
  • [10] Regiospecific synthesis of 1,4,5-trisubstituted-1,2,3-triazole via one-pot reaction promoted by copper(I) salt
    Wu, YM
    Deng, J
    Li, Y
    Chen, QY
    SYNTHESIS-STUTTGART, 2005, (08): : 1314 - 1318
12345