Handling Hazards Using Continuous Flow Chemistry: Synthesis of N1-Aryl-[1,2,3]-triazoles from Anilines via Telescoped Three-Step Diazotization, Azidodediazotization, and [3+2] Dipolar Cycloaddition Processes

被引：36

作者：

Teci, Matthieu ^{[1
]}

Tilley, Michael ^{[1
]}

McGuire, Michael A. ^{[2
]}

Organ, Michael G. ^{[1
,3
,4
]}

机构：

[1] York Univ, Dept Chem, 4700 Keele St, Toronto, ON M3J 1P3, Canada

[2] GlaxoSmithKline Pharmaceut Inc, 709 Swedeland Rd,POB 1539,UMW 2810, King Of Prussia, PA 19406 USA

[3] Univ Ottawa, CCRI, Ottawa, ON K1N 6N5, Canada

[4] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2016年 / 20卷 / 11期

基金：

加拿大自然科学与工程研究理事会;

关键词：

anilines; diazotization; triazoles; click chemistry; dipolar cycloaddition; flow; AZIDE-ALKYNE CYCLOADDITION; ORGANIC-SYNTHESIS MACOS; MULTICOMPONENT CLICK SYNTHESIS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; COPPER NANOPARTICLES; MULTISTEP SYNTHESIS; REACTOR TECHNOLOGY; CHEMICAL-SYNTHESIS; NATURAL-PRODUCTS; PROCESS WINDOWS;

D O I：

10.1021/acs.oprd.6b00292

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The conversion of commercially available anilines into triazole products was realized using a telescoped three-reactor flow diazotization, azidodediazotization, and [3 + 2] dipolar cycloaddition process. The diazotization azidodediazotization sequence was accelerated by means of an ultrasonic bath resulting in a degassed, segmented effluent. An automated continuous flow unit controlled by custom software created in-house was used to collect the aryl azide stream and restore it to a continuous column of the reagent. When combined with a variety of dipolarophiles, 1-aryl-[1,2,3]-triazoles were thus assembled by either copper catalyzed alkyne azide cycloaddition (CuAAC) or Huisgen cycloaddition reactions.

引用

页码：1967 / 1973

页数：7

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