Cu(I)-promoted one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and nitrobenzaldehydes

被引：4

作者：

Liu, Xia ^{[1
]}

Su, Changhui ^{[2
]}

机构：

[1] Jiangsu Open Univ, Coll Environm & Ecol, Nanjing 210036, Jiangsu, Peoples R China

[2] Nanjing Univ, Jinling Coll, Sch Chem & Life Sci, Nanjing, Jiangsu, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2017年 / 47卷 / 04期

基金：

中国国家自然科学基金;

关键词：

1,2,3-triazoles; anti-3-aryl-2,3-dibromopropanoic acid; click chemistry; one-pot; STEREOSELECTIVE-SYNTHESIS; TERMINAL ALKYNES; AZIDES; CYCLOADDITION;

D O I：

10.1080/00397911.2016.1262039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 1,4-disubstituted 1,2,3-triazoles were synthesized through a one-pot process from easily available anti-3-aryl-2,3-dibromopropanoic acids and nitrobenzaldehydes in hexamethylphosphoric triamide. Inexpensive copper(I) iodide was the catalyst.

引用

页码：279 / 284

页数：6

共 24 条

[1] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].

ALVAREZ, R ;

VELAZQUEZ, S ;

SANFELIX, A ;

AQUARO, S ;

DECLERCQ, E ;

PERNO, CF ;

KARLSSON, A ;

BALZARINI, J ;

CAMARASA, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194

[2] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[3] STUDIES ON 1,2,3-TRIAZOLES .13. (PIPERAZINYLALKOXY)[1]BENZOPYRANO[2,3-D]-1,2,3-TRIAZOL-9(1H)-ONES WITH COMBINED H-1 ANTIHISTAMINE AND MAST-CELL STABILIZING PROPERTIES [J].

BUCKLE, DR ;

ROCKELL, CJM ;

SMITH, H ;

SPICER, BA .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2262-2267

[4] Copper(I) Iodide Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from anti-3-Aryl-2,3-dibromopropanoic Acids and Organic Azides [J].

Cheng, Xuezhi ;

Yang, Yiwen ;

Kuang, Chunxiang ;

Yang, Qing .

SYNTHESIS-STUTTGART, 2011, (18) :2907-2912

[5] Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis [J].

Genin, MJ ;

Allwine, DA ;

Anderson, DJ ;

Barbachyn, MR ;

Emmert, DE ;

Garmon, SA ;

Graber, DR ;

Grega, KC ;

Hester, JB ;

Hutchinson, DK ;

Morris, J ;

Reischer, RJ ;

Ford, CW ;

Zurenko, GE ;

Hamel, JC ;

Schaadt, RD ;

Stapert, D ;

Yagi, BH .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :953-970

[6]

Heriberto D. V., 2014, ORG BIOMOL CHEM, V12, P9350

[7] Advances in the Construction of 1-Monosubstituted 1,2,3-Triazole Ring [J].

Jiang, Yubo ;

Han, Chunmei ;

Liang, Xueqiu ;

Yang, Peng ;

Wang, Hong .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (09) :1884-1890

[8] Copper(I) Iodide-Catalyzed Synthesis of 4-Aryl-1H-1,2,3-triazoles from anti-3-Aryl-2,3-dibromopropanoic Acids and Sodium Azide [J].

Jiang, Yubo ;

Kuang, Chunxiang ;

Yang, Qing .

SYNTHESIS-STUTTGART, 2010, (24) :4256-4260

[9] 4-Aryl-1,2,3-triazole: A novel template for a reversible methionine aminopeptidase 2 inhibitor, optimized to inhibit angiogenesis in vivo [J].

Kallander, LS ;

Lu, Q ;

Chen, WF ;

Tomaszek, T ;

Yang, G ;

Tew, D ;

Meek, TD ;

Hofmann, GA ;

Schulz-Pritchard, CK ;

Smith, WW ;

Janson, CA ;

Ryan, MD ;

Zhang, GF ;

Johanson, KO ;

Kirkpatrick, RB ;

Ho, TF ;

Fisher, PW ;

Mattern, MR ;

Johnson, RK ;

Hansbury, MJ ;

Winkler, JD ;

Ward, KW ;

Veber, DF ;

Thompson, SK .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (18) :5644-5647

[10]

Katritzky AR, 2003, HETEROCYCLES, V60, P1225

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