Metal-Free Three-Component Assembly of Fully Substituted 1,2,3-Triazoles

被引：16
|
作者：
Ahamad, Shakir [1 ,3 ]
Kumar, Anuj [1 ]
Kant, Ruchir [2 ]
Mohanan, Kishor [1 ,3 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India
[2] CSIR Cent Drug Res Inst, Mol & Struct Biol, Lucknow 226031, Uttar Pradesh, India
[3] Acad Sci & Innovat Res, New Delhi, India
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 08期
关键词：
cycloaddition; diazomethylsulfones; metal-free synthesis; three-component reactions; triazoles; BESTMANN-OHIRA REAGENT; AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; CATALYZED TRANSANNULATION; REGIOSPECIFIC SYNTHESIS; N-TOSYLHYDRAZONES; RAPID SYNTHESIS;
D O I：
10.1002/ajoc.201800340
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical domino three-component protocol involving aldehydes, amines, and alpha-diazo-beta-ketosulfones provides efficient access to fully substituted 1,2,3-triazoles. The process proceeds through a tandem Schiff-base formation and 1,3-dipolar cycloaddition to generate a key sulfonyltriazoline intermediate, which subsequently undergoes an oxidative aromatization with the aid of air or iodine. The three-component protocol obviates the need of expensive metal catalysts, proceeds under mildly basic conditions, and tolerates a wide range of synthetically useful (hetero)aryl and aliphatic aldehydes, and functionalized amines.
引用
收藏
页码：1698 / 1703
页数：6
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