Greener and Expeditious Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Terminal Acetylenes and in situ Generated α-Azido Ketones

被引：35

作者：

Kumar, Dalip ^{[1
]}

Patel, Gautam ^{[1
]}

Reddy, V. Buchi ^{[1
]}

机构：

[1] Birla Inst Technol & Sci, Chem Grp, Pilani 333031, Rajasthan, India

来源：

SYNLETT | 2009年 / 03期

关键词：

1,2,3-triazoles; alpha-bromo ketones; click chemistry; alpha-azido ketones; CLICK CHEMISTRY; ORGANIC-REACTIONS; REACTION MEDIA; ANALOGS; WATER;

D O I：

10.1055/s-0028-1087556

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and mild protocol for the one-pot regioselective synthesis of I,4-disubstituted 1,2,3-triazoles in aqueous PEG; 400 has been reported. The methodology involves the one-pot reaction of alpha-bromo ketones, sodium azide, and terminal acetylenes catalyzed by Cu(I) in aqueous PEG 400 at room temperature. Prominent features of our approach are mild reaction conditions, use of readily available alpha-bromo compounds, aqueous PEG 400 as a benign reaction medium, avoiding the isolation of labile alpha-azido ketones, simple workup, and good yields.

引用

页码：399 / 402

页数：4

共 39 条

[31] [3+2] Cycloaddition of acetylenes with azides to give 1,4-disubstituted 1,2,3-triazoles in a modular flow reactor [J].

Smith, Christopher D. ;

Baxendale, Ian R. ;

Lanners, Steve ;

Hayward, John J. ;

Smith, Stephen C. ;

Ley, Steven V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (10) :1559-1561

[32]

Smith P.A. S., 1983, Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, P263

[33] Profiling enzyme activities in vivo using click chemistry methods [J].

Speers, AE ;

Cravatt, BF .

CHEMISTRY & BIOLOGY, 2004, 11 (04) :535-546

[34] A mild and efficient procedure for α-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate [J].

Tanemura, K ;

Suzuki, T ;

Nishida, Y ;

Satsumabayashi, K ;

Horaguchi, T .

CHEMICAL COMMUNICATIONS, 2004, (04) :470-471

[35] A versatile new monomer family:: Functionalized 4-vinyl-1,2,3-triazoles via click chemistry [J].

Thibault, Raymond J. ;

Takizawa, Kenichi ;

Lowenheilm, Peter ;

Helms, Brett ;

Mynar, Justin L. ;

Frechet, Jean M. J. ;

Hawker, Craig J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (37) :12084-12085

[36] Regiospecific synthesis and anti-human immunodeficiency virus activity of novel 5-substituted N-alkylcarbamoyl and N,N-dialkyl carbamoyl 1,2,3-triazole-TSAO analogues [J].

Velázquez, S ;

Alvarez, R ;

Pérez, C ;

Gago, F ;

De Clercq, E ;

Balzarini, J ;

Camarasa, MJ .

ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1998, 9 (06) :481-489

[37]

Yalkowsky SH, 1992, AQUEOUS SOLUBILITY M

[38]

Zaslavsky B.Y., 1994, Aqueous Two-Phase Partitioning: Physical Chemistry and Bioanalytical Applications

[39]

Zhu J, 2005, MULTICOMPONENT REACTIONS, P1, DOI 10.1002/3527605118

← 1 2 3 4 →