Straightforward synthesis of enantiomerically pure 1,2,3-triazoles derived from amino esters

被引：16

作者：

Silveira-Dorta, Gaston ^{[1
]}

Jana, Sampad ^{[1
]}

Borkova, Lucie ^{[2
]}

Thomas, Joice ^{[1
]}

Dehaen, Wim ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Dept Chem, Mol Design & Synth, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[2] Palacky Univ Olomouc, Fac Med & Dent, Inst Mol & Translat Med, Hnevotinska 1333-5, Olomouc 77900, Czech Republic

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 17期

关键词：

ACID; CYCLOADDITION; KETONES; ALKYNES; AZIDES;

D O I：

10.1039/c8ob00533h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and straightforward approach that enables, for the first time, the synthesis of enantiomerically pure 1,4,5-trisubstituted, 1,5-disubstituted, and fused 1,2,3-triazole derivatives has been developed. The synthesis employs enantiomerically pure amino esters derived from amino acids and commercially available ketones under metal-free conditions.

引用

页码：3168 / 3176

页数：9

共 28 条

[1] The Rich Chemistry Resulting from the 1,3-Dipolar Cycloaddition Reactions of Enamines and Azides [J].

Bakulev, Vasiliy A. ;

Beryozkina, Tetyana ;

Thomas, Joice ;

Dehaen, Wim .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (03) :262-294

[2]

BIANCHETTI G, 1965, TETRAHEDRON LETT, P2043

[3] A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles [J].

Cheng, Guolin ;

Zeng, Xiaobao ;

Shen, Jinhai ;

Wang, Xuesong ;

Cui, Xiuling .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) :13265-13268

[4] Application of click chemistry on preparation of separation materials for liquid chromatography [J].

Chu, Changhu ;

Liu, Renhua .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2177-2188

[5]

Finn M.G., 2010, Chem. Soc. Rev, V39, P1221

[6] Copper toxicity, oxidative stress, and antioxidant nutrients [J].

Gaetke, LM ;

Chow, CK .

TOXICOLOGY, 2003, 189 (1-2) :147-163

[7] Design, synthesis, and biological activity of novel triazole amino acids used to probe binding interactions between ligand and neutral amino acid transport protein SN1 [J].

Gajewski, Mariusz ;

Seaver, Ben ;

Esslinger, C. Sean .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (15) :4163-4166

[8]

Hill M., 2011, DIMROTH TRIAZOLE SYN

[9] Probing the Bioactive Conformation of an Archetypal Natural Product HDAC Inhibitor with Conformationally Homogeneous Triazole-Modified Cyclic Tetrapeptides [J].

Horne, W. Seth ;

Olsen, Christian A. ;

Beierle, John M. ;

Montero, Ana ;

Ghadiri, M. Reza .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (26) :4718-4724

[10] 1.3-DIPOLARE CYCLOADDITIONEN .14. DIE ANLAGERUNG ORGANISCHER AZIDE AN ENOLATHER - ORIENTIERUNG UND TRIAZOLIN-ZERFALL [J].

HUISGEN, R ;

MOBIUS, L ;

SZEIMIES, G .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (04) :1138-&

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