Synthesis of α-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles

被引:0
作者
Vasconcelos, Stanley N. S. [1 ]
Fornari, Evelin [1 ]
Caracelli, Ignez [2 ]
Stefani, Helio A. [1 ]
机构
[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP, Brazil
[2] Univ Fed Sao Carlos, Dept Fis, Sao Carlos, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Multicomponent reaction; MRC; Ugi reaction; Click chemistry; Triazole; Flow chemistry; MULTICOMPONENT REACTIONS; ORGANIC-SYNTHESIS; (-)-LEMONOMYCIN; PEPTOIDS; ACIDS;
D O I
10.1007/s11030-017-9764-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The Ugi multicomponent reaction has been used as an important synthetic route to obtain compounds with potential biological activity. We present the rapid and efficient synthesis of -amino-1,3-dicarbonyl compounds in moderate to good yields via Ugi flow chemistry reactions performed with a continuous flow reactor. Such -amino-1,3-dicarbonyl compounds can act as precursors for the production of -amino acids via hydrolysis of the ethyl ester group as well as building blocks for the synthesis of novel compounds with the 1,2,3-triazole ring. The -amino acid derivatives of the Ugi flow chemistry reaction products were then used for dipeptide synthesis.
引用
收藏
页码:893 / 902
页数:10
相关论文
共 25 条
[1]   Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation [J].
Ambreen, Nida ;
Kumar, Ravi ;
Wirth, Thomas .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :1437-1442
[2]   The total synthesis of (-)-lemonomycin [J].
Ashley, ER ;
Cruz, EG ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (49) :15000-15001
[3]   One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor [J].
Bagley, Mark C. ;
Fusillo, Vincenzo ;
Jenkins, Robert L. ;
Lubinu, M. Caterina ;
Mason, Christopher .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :1957-1968
[4]   Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions [J].
Barreto, Angelica de Fatima S. ;
Vercillo, Otilie E. ;
Birkett, Mike A. ;
Caulfield, John C. ;
Wessjohann, Ludger A. ;
Andrade, Carlos Kleber Z. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) :5024-5027
[5]   Higher-order multicomponent reactions: beyond four reactants [J].
Brauch, Sebastian ;
van Berkel, Sander S. ;
Westermann, Bernhard .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :4948-4962
[6]   Multicomponent reactions: advanced tools for sustainable organic synthesis [J].
Cioc, Razvan C. ;
Ruijter, Eelco ;
Orru, Romano V. A. .
GREEN CHEMISTRY, 2014, 16 (06) :2958-2975
[7]   Enantioselective total synthesis of ecteinascidin 743 [J].
Corey, EJ ;
Gin, DY ;
Kania, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203
[8]   A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitor Atazanavir [J].
Dalla-Vechia, Luciana ;
Reichart, Benedikt ;
Glasnov, Toma ;
Miranda, Leandro S. M. ;
Kappe, C. Oliver ;
de Souza, Rodrigo O. M. A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (39) :6806-6813
[9]   Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis [J].
Fanelli, Flavio ;
Parisi, Giovanna ;
Degennaro, Leonardo ;
Luisi, Renzo .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 :520-542
[10]   Continuous-Flow TechnologyA Tool for the Safe Manufacturing of Active Pharmaceutical Ingredients [J].
Gutmann, Bernhard ;
Cantillo, David ;
Kappe, C. Oliver .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (23) :6688-6728