Efficient Synthesis of (1,2,3-Triazol-1-yl)methylpyrimidines from 5-Bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one

被引：12

作者：

Aquino, Estefania da C. ^{[1
]}

Lobo, Marcio M. ^{[1
]}

Leonel, Guilherme ^{[1
]}

Martins, Marcos A. P. ^{[1
]}

Bonacorso, Helio G. ^{[1
]}

Zanatta, Nilo ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 02期

关键词：

Nitrogen heterocycles; Pyrimidines; 1,2,3-Triazoles; Trifluoromethyl enones; Cyclization; Click chemistry; 6-METHYLENE-BRIDGED URACIL DERIVATIVES; HUMAN THYMIDINE PHOSPHORYLASE; INHIBITORS; AMINES; ETHERS;

D O I：

10.1002/ejoc.201601234

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one was used as an efficient precursor for the synthesis of a new series of (1,2,3-triazol-1-yl)methyl-pyrimidine biheterocycles. For this stepwise synthesis, the 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one was first converted into 5-azido-1,1,1-trifluoro-4-methoxypent-3-en-2-one through a nucleophilic substitution of the bromine by an azide group. This was then followed by an azide-alkyne cycloaddition reaction (click chemistry) to give the key intermediate 5-[4-alkyl(aryl)-1H-1,2,3-triazol-1-yl]-1,1,1-trifluoro-4-methoxypent-3-en-2-ones. These were cyclocondensed with 2-methylisothiourea sulfate to give a series of 2-(methylthio)-4-(1,2,3-triazol-1-yl)methyl-6-(trifluoromethyl)pyrimidines. Additionally, the 2-methylthiopyrimidine products were used to prepare a new series of 2-amino-4-(1,2,3-triazol-1-yl)methyl-6-(trifluoromethyl)pyrimidines.

引用

页码：306 / 312

页数：7

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