General Solution to the Synthesis of N-2-Substituted 1,2,3-Triazoles

被引：92

作者：

Wang, Xiao-Jun ^{[1
]}

Zhang, Li ^{[1
]}

Krishnamurthy, Dhileepkumar ^{[1
]}

Senanayake, Chris H. ^{[1
]}

Wipf, Peter ^{[2
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA

[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 20期

关键词：

EFFICIENT SYNTHESIS; TERMINAL ALKYNES; CLICK CHEMISTRY; CYCLOADDITION; AZIDES; ALKYLATION; SCOPE; ACID;

D O I：

10.1021/ol101965a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselective N-alkylation of 1,2,3-triazoles 1-6 was studied Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5-trimethylsilyl-1,2,3-triazoles These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10-15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds

引用

页码：4632 / 4635

页数：4

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