Stereo- and regio-selective one-pot synthesis of triazole-based unnatural amino acids and β-amino triazoles

被引:45
作者
Baig, R. B. Nasir [1 ]
Varma, Rajender S. [1 ]
机构
[1] US EPA, Sustainable Technol Div, Natl Risk Management Res Lab, Cincinnati, OH 45268 USA
关键词
CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; MEDICINAL CHEMISTRY; FACILE ENTRY; SOLID-PHASE; MICROWAVE; SULFAMIDATE; AZIDES; HETEROCYCLES; REACTIVITY;
D O I
10.1039/c2cc32392c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of triazole based unnatural amino acids and beta-amino triazoles has been described via a stereo and regioselective one-pot multi-component reaction of sulfamidates, sodium azide, and alkynes under MW conditions. The developed method is applicable to a broad substrate scope and has significant potential for the synthesis of unnatural amino acids with a triazole side chain.
引用
收藏
页码:5853 / 5855
页数:3
相关论文
共 56 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]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[3]   N-(9-(9-phenylfluorenyl))homoserine-derived cyclic sulfamidates:: Novel chiral educts for the synthesis of enantiopure γ-substituted α-amino acids [J].
Atfani, M ;
Wei, L ;
Lubell, WD .
ORGANIC LETTERS, 2001, 3 (19) :2965-2968
[4]   Facile Synthesis of β-Amino Disulfides, Cystines, and Their Direct Incorporation into Peptides [J].
Baig, Nasir R. B. ;
Kanimozhi, Catherine K. ;
Sudhir, V. Sai ;
Chandrasekaran, Srinivasan .
SYNLETT, 2009, (08) :1227-1232
[5]   Synthesis of Unnatural Selenocystines and β-Aminodiselenides via Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot, Multistep Strategy [J].
Baig, Nasir Rashid Baig ;
Chandrakala, R. N. ;
Sudhir, V. Sai ;
Chandrasekaran, Srinivasan .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2910-2921
[6]   Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1559-1584
[7]   Synthesis of amino thiols and isocysteines via regioselective ring opening of sulfamidates with tetrathiomolybdate [J].
Baig, R. B. Nasir ;
Kumar, N. Y. Phani ;
Mannuthodikayil, Jamsad ;
Chandrasekaran, Srinivasan .
TETRAHEDRON, 2011, 67 (17) :3111-3118
[8]   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
[9]   Cyclic sulfamidates as vehicles for the synthesis of substituted lactams [J].
Bower, JF ;
Svenda, J ;
Williams, AJ ;
Charmant, JPH ;
Lawrence, RM ;
Szeto, P ;
Gallagher, T .
ORGANIC LETTERS, 2004, 6 (25) :4727-4730
[10]   N-Heterocycle construction via cyclic sulfamidates. Applications in synthesis [J].
Bower, John F. ;
Rujirawanicha, Janjira ;
Gallagher, Timothy .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (07) :1505-1519