A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1H-1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide

被引：16

作者：

Wu, Guang-Long ^{[1
]}

Wu, Qin-Pei ^{[1
]}

机构：

[1] Beijing Inst Technol, Sch Chem & Chem Engn, 5 South Zhongguancun St, Beijing 100081, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 14期

基金：

中国国家自然科学基金;

关键词：

phosphonium salt; triazole; organic catalyst; multicomponent reaction; cycloaddition; SITU CLICK CHEMISTRY; ONE-POT SYNTHESIS; BIFUNCTIONAL POLYMERIC REAGENT; SOLID-PHASE SYNTHESIS; WITTIG REACTION; 1,3-DIPOLAR CYCLOADDITION; FUNCTIONALIZED 1,2,3-TRIAZOLES; ALKYNE CYCLOADDITION; 3-COMPONENT REACTION; MEDICINAL CHEMISTRY;

D O I：

10.1055/s-0037-1609720

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and metal-free multi-component reaction to synthesize 4,5-disubstituted 1H-1,2,3-triazoles from phosphonium salts, aldehydes, and sodium azide is described. The process undergoes an organocatalyzed coupling of formyl group with phosphonium to form a key intermediate, olefinic phosphonium salt, which is followed by the [3+2] cycloaddition of the azide to the activated alkene. A series of representative 4,5-disubstituted 1H-1,2,3-triazoles were prepared.

引用

页码：2768 / 2774

页数：7

共 72 条

[1] Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3+2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions [J].

Amantini, D ;

Fringuelli, F ;

Piermatti, O ;

Pizzo, F ;

Zunino, E ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6526-6529

[2]

Angelos S., 2008, ANGEW CHEM INT EDIT, V45, P1435

[3] Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures [J].

Aucagne, V ;

Hänni, KD ;

Leigh, DA ;

Lusby, PJ ;

Walker, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2186-2187

[4] Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry [J].

Aucagne, Vincent ;

Leigh, David A. .

ORGANIC LETTERS, 2006, 8 (20) :4505-4507

[5] α-Haloacrylates as acceptors in the [3+2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates [J].

Augustine, John Kallikat ;

Boodappa, Chandrakantha ;

Venkatachaliah, Srinivasa .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (14) :2280-2288

[6]

BAZHENOV DN, 1994, ZH ORG KHIM+, V30, P791

[7] Geminally activated nitroethenes in reactions with sodium azide. Synthesis of functionalized 1,2,3-triazoles [J].

Berestovitskaya, V. M. ;

Baichurin, R. I. ;

Aboskalova, N. I. ;

Baichurina, L. V. ;

Trukhin, E. V. ;

Fel'gendler, A. V. ;

Gensirovskaya, M. A. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (06) :1266-1273

[8] Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism [J].

Boren, Brant C. ;

Narayan, Sridhar ;

Rasmussen, Lars K. ;

Zhang, Li ;

Zhao, Haitao ;

Lin, Zhenyang ;

Jia, Guochen ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8923-8930

[9] The modern interpretation of the Wittig reaction mechanism [J].

Byrne, Peter A. ;

Gilheany, Declan G. .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (16) :6670-6696

[10] Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins' Bicyclic Sugar Moiety [J].

Cachatra, Vasco ;

Almeida, Andreia ;

Sardinha, Joao ;

Lucas, Susana D. ;

Gomes, Ana ;

Vaz, Pedro D. ;

Florencio, M. Helena ;

Nunes, Rafael ;

Vila-Vicosa, Diogo ;

Calhorda, Maria Jose ;

Rauter, Amelia P. .

ORGANIC LETTERS, 2015, 17 (22) :5622-5625

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