"Click" Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)

被引：49

作者：

Aizpurua, Jesus M. ^{[1
]}

Azcune, Itxaso ^{[1
]}

Fratila, Raluca M. ^{[2
]}

Balentova, Eva ^{[1
]}

Sagartzazu-Aizpurua, Maialen ^{[1
]}

Miranda, Jose I.

机构：

[1] Univ Basque Country, Dept Quim Organ 1, Joxe Mari Korta R&D Ctr, San Sebastian 20018, Spain

[2] Univ Twente, Fac Sci & Technol, NL-7500 AE Enschede, Netherlands

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 07期

关键词：

ONE-POT; 1,3-DIPOLAR CYCLOADDITIONS; MEDICINAL CHEMISTRY; TRIAZOLE OLIGOMERS; TERMINAL ALKYNES; SOLID-PHASE; AZIDES; LIGATION;

D O I：

10.1021/ol1003127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unsymmetrically 1,1'-disubstituted 4,4'-bis-1H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole intermediates 5: (a) the stepwise Swern oxidation/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadlyne 9. The method is highlighted by its compatibility with orthogonally protected and functionalized saccharide-peptide hybrids and its ability to be extended to the trisubstituted counterparts 12.

引用

页码：1584 / 1587

页数：4

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