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

页码：2891 / 2897

页数：7

共 50 条

[41] 4-(Boc-amino)-1H-1,2,3-triazole-5-carboxylic acids - convenient reagents for the synthesis of 1,4,6,7-tetrahydro[1,2,3]triazolo[4,5-e][1,4]diazepine-5,8-diones
Syrota, Natalia A.
Kemskiy, Sergiy V.
Bol'but, Andriy V.
Vovk, Mikhailo V.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (11) : 1092 - 1097
[42] The structural properties of 5-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid and chromogenic mechanism on its rhodamine B derivatives to Hg2+ ions
Li, Jianling
Ding, Guohua
Niu, Yanyan
Wu, Luyong
Feng, Huajie
He, Wenying
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2018, 200 : 127 - 135
[43] 1-(2-aminophenyl)-1H-1,2,3-triazole-4-carboxylic acid: activity against Gram-positive and Gram-negative pathogens including Vibrio cholerae
Maji, Krishnendu
Haldar, Debasish
ROYAL SOCIETY OPEN SCIENCE, 2017, 4 (10):
[44] Derivatives of 4-Amino- and 4-Ureido-2-phenyl-1,2,3-triazole-5-carboxylic Acid 1-Oxides
A. A. Yavolovskii
O. A. Oliinichenko
V. D. Kirpichenko
E. I. Ivanov
Russian Journal of General Chemistry, 2005, 75 : 636 - 638
[45] In-Water Synthesis of 5-Thiolated 1,2,3-Triazoles from β-Thioenaminones by Diazo Transfer Reaction
Deng, Leiling
Cao, Xiaoji
Liu, Yunyun
Wan, Jie-Ping
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21): : 14179 - 14186
[46] THE MECHANISM OF THE TAUTOMERIC CHANGE OF 5-HYDROXY-1-2-3-TRIAZOLE-4-CARBOXYLIC ESTERS INTO ALIPHATIC DIAZO-COMPOUNDS
BROWN, BR
HAMMICK, DL
JOURNAL OF THE CHEMICAL SOCIETY, 1947, (OCT): : 1384 - 1386
[47] Derivatives of 4-amino- and 4-ureido-2-phenyl-1,2,3-triazole-5-carboxylic acid 1-oxides
Yavolovskii, AA
Oliinichenko, OA
Kirpichenko, VD
Ivanov, EI
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2005, 75 (04) : 636 - 638
[48] An Efficient and Convenient Synthesis of Ethyl 1-(4-Methoxyphenyl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate
Chen, Jung-Hsuan
Liu, Shuan-Ru
Chen, Kwunmin
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (02) : 328 - 333
[49] A simple and convenient synthesis of 3-[5-(trifluoromethyl)-1,2,3-triazol-4-yl]cinnamic acids from 4-aryl-6-(trifluoromethyl)-2H-pyran-2-ones and sodium azide
Usachev, Boris I.
Usachev, Sergey A.
Roeschenthaler, Gerd-Volker
Sosnovskikh, Vyacheslav Ya
TETRAHEDRON LETTERS, 2011, 52 (50) : 6723 - 6725
[50] SYNTHESIS OF 4-KETO SUBSTITUTED 1-ALKYL-1,2,3-TRIAZOLES FROM 5-SUBSTITUTED 1-PHENYL-1,2,3-TRIAZOLE-4-CARBALDEHYDES
LABBE, G
VANESSCHE, G
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1991, 100 (04): : 289 - 290

← 1 2 3 4 5 →