Manganese(II) chloride catalyzed highly efficient one-pot synthesis of propargylamines and fused triazoles via three-component coupling reaction under solvent-free condition

被引：39

作者：

Afraj, Shakil N. ^{[1
]}

Chen, Chinpiao ^{[1
]}

Lee, Gene-Hsian ^{[2
]}

机构：

[1] Natl Dong Hwa Univ, Dept Chem, Soufeng 974, Hualien, Taiwan

[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 10617, Taiwan

来源：

RSC ADVANCES | 2014年 / 4卷 / 50期

关键词：

C-H ACTIVATION; AZIDE-ALKYNE CYCLOADDITION; TERMINAL ALKYNES; CLICK-CHEMISTRY; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; ASYMMETRIC-SYNTHESIS; DIRECT ADDITION; ALDEHYDE; AMINE;

D O I：

10.1039/c4ra03232b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot green and highly efficient method for the synthesis of propargylamines and diastereoselective synthesis of fused triazoles via three-component coupling in the presence of manganese(II) chloride as a catalyst and a catalyst-free 1,3-dipolar cycloaddition reaction, respectively, without using a co-catalyst or activator is reported. This methodology is efficient, eco-friendly, operationally simple and effective for reactions involving aromatic, aliphatic, and heterocyclic aldehydes, and provides an easy access to propargylamines in excellent yields, fused triazoles in good yield and excellent diastereoselectivities.

引用

页码：26301 / 26308

页数：8

共 127 条

[1] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].

Agard, NJ ;

Prescher, JA ;

Bertozzi, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047

[2]

Alami M, 1998, SYNLETT, P325

[3] 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

[4]

[Anonymous], 2010, GREEN CHEM

[5] HIGHLY DIASTEREOSELECTIVE REACTION OF A CHIRAL, NON-RACEMIC AMIDE ENOLATE WITH (S)-GLYCIDYL TOSYLATE - SYNTHESIS OF THE ORALLY-ACTIVE HIV-1 PROTEASE INHIBITOR L-735,524 [J].

ASKIN, D ;

ENG, KK ;

ROSSEN, K ;

PURICK, RM ;

WELLS, KM ;

VOLANTE, RP ;

REIDER, PJ .

TETRAHEDRON LETTERS, 1994, 35 (05) :673-676

[6] KINETIC DETECTION OF IMMINIUM CATION IN FORMALDEHYDE-AMINE CONDENSATIONS IN NEUTRAL AQUEOUS SOLUTION [J].

BENKOVIC, SJ ;

BENKOVIC, PA ;

COMFORT, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (07) :1860-&

[7] 1,2,3-triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a][1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding [J].

Bertelli, L ;

Biagi, G ;

Giorgi, I ;

Livi, O ;

Manera, C ;

Scartoni, V ;

Martini, C ;

Giannaccini, G ;

Trincavelli, L ;

Barili, PL .

FARMACO, 1998, 53 (04) :305-311

[8] Enantioselective one-pot three-component synthesis of propargylamines [J].

Bisai, Alakesh ;

Singh, Vinod K. .

ORGANIC LETTERS, 2006, 8 (11) :2405-2408

[9] Regioselective Intramolecular Dipolar Cycloaddition of Azides and Unsymmetrical Alkynes [J].

Brawn, Ryan A. ;

Welzel, Morgan ;

Lowe, Jason T. ;

Panek, James S. .

ORGANIC LETTERS, 2010, 12 (02) :336-339

[10] 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

← 1 2 3 4 5 6 7 8 9 10 →