A Convenient Route to 1-Alkyl-5-trifluoromethyl-1,2,3-triazole-4-carboxylic Acids Employing a Diazo Transfer Reaction

被引：15
|
作者：
Iminov, Rustam T. [1 ]
Mashkov, Alexander V. [1 ]
Chalyk, Bohdan A. [2 ]
Mykhailiuk, Pavel K. [1 ,2 ]
Tverdokhlebov, Anton V. [1 ,2 ]
Tolmachev, Andrey A. [1 ,2 ]
Volovenko, Yulian M. [1 ]
Shishkin, Oleg V. [3 ]
Shishkina, Svetlana V. [3 ]
机构：
[1] Kiev Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine
[2] Enamine Ltd, UA-01103 Kiev, Ukraine
[3] NAS Ukraine, Inst Single Crystals, STC, UA-61001 Kharkov, Ukraine
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 14期
关键词：
Synthetic methods; Medicinal chemistry; Nitrogen heterocycles; Amines; Azides; Fluorine; BETA-AMINO ACIDS; EFFICIENT SYNTHESIS; 5-FLUOROALKYLATED 1H-1,2,3-TRIAZOLES; BROMODIFLUOROMETHYLATED TRIAZOLE; 1,2,3-TRIAZOLE DERIVATIVES; 1,3-DIPOLAR CYCLOADDITION; FLUORINE; AZIDE; REGIOSELECTIVITY; RUFINAMIDE;
D O I：
10.1002/ejoc.201300030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of ethyl 3-(alkylamino)-4,4,4-trifluoro-but-2-enoates with mesyl azide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave ethyl 1-alkyl-5-trifluoromethyl-1,2,3-triazole-4-carboxylates in good yields. Further hydrolysis of the ester group afforded the title compounds on a multigram scale.
引用
收藏
页码：2891 / 2897
页数：7
相关论文
共 50 条
  • [1] Convenient synthesis of 1-norbornyl-5-R-1H-1,2,3-triazole-4-carboxylic acids
    Pokhodylo, N. T.
    Matiichuk, V. S.
    Obushak, M. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (03) : 481 - 483
  • [2] Convenient synthesis of 1-norbornyl-5-R-1H-1,2,3-triazole-4-carboxylic acids
    N. T. Pokhodylo
    V. S. Matiichuk
    M. D. Obushak
    Russian Journal of Organic Chemistry, 2017, 53 : 481 - 483
  • [3] 1-Benzyl-5-methyl-1H-1,2,3-triazole-4-carboxylic acid
    Wang, Gai-Gai
    Zhao, Hong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O322 - U2001
  • [4] 5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid
    Lin, Jin Rui
    Yao, Ji Yuan
    Zhao, Hong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1843 - U2700
  • [5] 1-Benzyl-5-methyl-1H-1,2,3-triazole-4-carboxylic acid monohydrate
    Zhao, Hong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1258 - U1675
  • [6] Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series
    Pokhodylo, Nazariy T.
    Obushak, Mykola D.
    MOLBANK, 2022, 2022 (03)
  • [7] Preparation of Quinoline-2,4-dione Functionalized 1,2,3-Triazol-4-ylmethanols, 1,2,3-Triazole-4-carbaldehydes and 1,2,3-Triazole-4-carboxylic Acids
    Milicevic, David
    Kimmel, Roman
    Urankar, Damijana
    Pevec, Andrej
    Kosmrlj, Janez
    Kafka, Stanislav
    ACTA CHIMICA SLOVENICA, 2020, 67 (02) : 421 - 434
  • [8] Bis(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid) monohydrate
    Lin, Jin Rui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1967 - U754
  • [9] Crystal structure of 1-anilino-5-methyl-1H-1,2,3-triazole-4-carboxylic acid monohydrate
    Moreira, Olivia B. O.
    Freitas, Maria Clara R.
    Souza, Karynne C.
    Jordao, Alessandro K.
    Resende, Jackson A. L. C.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 : 738 - +
  • [10] 5-Methyl-1-(3-nitrobenzyl)-1H-1,2,3-triazole-4-carboxylic acid monohydrate
    Xiao, Jie
    Wang, Wen Xiang
    Zhao, Hong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O2085 - U1623
12345