Preparation of 4,5 disubstituted-2H-1,2,3-triazoles from (Z)-2,3-diaryl substituted acrylonitriles

被引:11
作者
Madadi, Nikhil Reddy [1 ]
Penthala, Narsimha Reddy [1 ]
Song, Lin [1 ]
Hendrickson, Howard P. [1 ]
Crooks, Peter A. [1 ]
机构
[1] Univ Arkansas Med Sci, Coll Pharm, Dept Pharmaceut Sci, Little Rock, AR 72205 USA
关键词
Sodium azide; Triazole synthesis; Acrylonitrile; Huisgen cycloaddition; ANALOGS; AGENTS;
D O I
10.1016/j.tetlet.2014.05.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2H-1,2,3-Triazoles (2) were synthesized by [3+2] cycloaddition of (Z)-2,3-diaryl substituted acrylonitriles (1) with sodium azide and ammonium chloride in DMF/water. This method represents a facile and efficient reaction procedure for the synthesis of 4,5-diary1-2H-1,2,3-triazoles in modest to good yields. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4207 / 4211
页数:5
相关论文
共 18 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]   In vitro and in vivo biological evaluation of new 4,5-disubstituted 1,2,3-triazoles as cis-constrained analogs of combretastatin A4 [J].
Blanch, Nuria Mur ;
Chabot, Guy G. ;
Quentin, Lionel ;
Scherman, Daniel ;
Bourg, Stephane ;
Dauzonne, Daniel .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 :22-32
[3]  
Cai D., 2000, U.S. Patent, Patent No. [US 6051707, 6051707]
[4]   Combretazet-3 a novel synthetic cis-stable combretastatin A-4-azetidinone hybrid with enhanced stability and therapeutic efficacy in colon cancer [J].
Greene, Lisa M. ;
Wang, Shu ;
O'Boyle, Niamh M. ;
Bright, Sandra A. ;
Reid, Jane E. ;
Kelly, Patrick ;
Meegan, Mary J. ;
Zisterer, Daniela M. .
ONCOLOGY REPORTS, 2013, 29 (06) :2451-2458
[5]   Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited [J].
Krasinski, A ;
Fokin, VV ;
Sharpless, KB .
ORGANIC LETTERS, 2004, 6 (08) :1237-1240
[6]   A study of the scope and regioselectivity of the ruthenium-catalyzed [3+2]-cycloaddition of azides with internal alkynes [J].
Majireck, Max M. ;
Weinreb, Steven M. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8680-8683
[7]  
Morgan N. H., 1991, Eur. Pat. Appl., Patent No. [EP 437979, A2, 437979]
[8]  
Morgan N. H., 1991, Eur. Pat. Appl., Patent No. [EP 19910724, 19910724]
[9]   Rufinamide:: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy [J].
Pålhagen, S ;
Canger, R ;
Henriksen, O ;
van Parys, JA ;
Rivière, ME ;
Karolchyk, MA .
EPILEPSY RESEARCH, 2001, 43 (02) :115-124
[10]   Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents [J].
Penthala, Narsimha Reddy ;
Sonar, Vijayakumar N. ;
Horn, Jamie ;
Leggas, Markos ;
Yadlapalli, Jai Shankar K. B. ;
Crooks, Peter A. .
MEDCHEMCOMM, 2013, 4 (07) :1073-1078