Synthesis of Tetrasubstituted Pyrazoles from Substituted Hydrazines and β-Keto Esters

被引:13
作者
Bakanas, Ian J. [1 ]
Moura-Letts, Gustavo [1 ]
机构
[1] Rowan Univ, Dept Chem & Biochem, 201 Mullica Hill Rd, Glassboro, NJ 08028 USA
关键词
Tetrasubstituted pyrazoles; Pyrazolones; Nitrogen heterocycles; Cyclization; Reaction mechanisms; ONE-POT SYNTHESIS; ROOM-TEMPERATURE SYNTHESIS; BASE-MEDIATED REACTION; REGIOSELECTIVE SYNTHESIS; ESTROGEN-RECEPTOR; PROMOTED SYNTHESIS; N-ARYLPYRAZOLES; BUILDING-BLOCKS; DERIVATIVES; LIGANDS;
D O I
10.1002/ejoc.201601093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report the synthesis of tetrasubstituted pyrazoles from simple hydrazines and beta-keto esters under mild, basic conditions. This reaction enables the selective synthesis of pyrazolones, alkoxypyrazoles, and tetrasubstituted pyrazoles for a large variety of aromatic hydrazines and substituted beta-keto esters with high yields and selectivities. This method permits access to highly complex pyrazole scaffolds with four orthogonal diversification groups.
引用
收藏
页码:5345 / 5349
页数:5
相关论文
共 61 条
  • [1] [Anonymous], 1975, ANGEW CHEM
  • [2] Interceptive [4+1] Annulation of in Situ Generated 1,2-Diaza-1,3-dienes with Diazo Esters: Direct Access to Substituted Mono-, Bi-, and Tricyclic 4,5-Dihydropyrazoles
    Attanasi, Orazio A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Mantellini, Fabio
    Mantenuto, Serena
    Nicolini, Simona
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) : 8331 - 8338
  • [3] Synthesis of Substituted Pyrazoles via Tandem Cross-Coupling/Electrocyclization of Enol Triflates and Diazoacetates
    Babinski, David J.
    Aguilar, Hector R.
    Still, Raymond
    Frantz, Doug E.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15) : 5915 - 5923
  • [4] Diastereoselective synthesis of substituted diaziridines from simple ketones and aldehydes
    Beebe, Alexander W.
    Dohmeier, Emma F.
    Moura-Letts, Gustavo
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (70) : 13511 - 13514
  • [5] Novel pyrazole derivatives as potential promising anti-inflammatory antimicrobial agents
    Bekhit, AA
    Ashour, HMA
    Guemei, AA
    [J]. ARCHIV DER PHARMAZIE, 2005, 338 (04) : 167 - 174
  • [6] NEW ULTRAVIOLET STABILIZERS - 3-(2'-HYDROXYPHENYL)PYRAZOLE AND 5-(2'-HYDROXYPHENYL)PYRAZOLE
    CATALAN, J
    FABERO, F
    CLARAMUNT, RM
    MARIA, MDS
    FOCESFOCES, MDC
    CANO, FH
    MARTINEZRIPOLL, M
    ELGUERO, J
    SASTRE, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 5039 - 5048
  • [7] A fascinating decade for the synthesis of 1,2-azoles
    Chakroborty, Subhendu
    Bhanja, Chittaranjan
    Jena, Satyaban
    [J]. HETEROCYCLIC COMMUNICATIONS, 2013, 19 (02) : 79 - 87
  • [8] Synthesis of Pyrazoles, Diazepines, Enaminones, and Enamino Esters Using 12-Tungstophosphoric Acid as a Reusable Catalyst in Water
    Chen, Xiang
    She, Jin
    Shang, Zhicai
    Wu, Jun
    Wu, Haifeng
    Zhang, Peizhi
    [J]. SYNTHESIS-STUTTGART, 2008, (21): : 3478 - 3486
  • [9] Room-Temperature Synthesis of Pyrazoles, Diazepines, β-Enaminones, and β-Enamino Esters Using Silica-Supported Sulfuric Acid as a Reusable Catalyst Under Solvent-Free Conditions
    Chen, Xiang
    She, Jin
    Shang, Zhi-Cai
    Wu, Jun
    Zhang, Peizhi
    [J]. SYNTHETIC COMMUNICATIONS, 2009, 39 (06) : 947 - 957
  • [10] Rutile Promoted Synthesis of Sulfonylamidonitriles from Simple Aldehydes and Sulfonamides
    Costantini, Nicholas V.
    Bates, Alex D.
    Haun, Graham J.
    Chang, Natasha M.
    Moura-Letts, Gustavo
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (04): : 1906 - 1911