Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence

被引：25

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Aragoncillo, Cristina ^{[1
]}

Callejo, Ricardo ^{[1
]}

Pilar Ruiz, M. ^{[1
]}

Rosario Torres, M. ^{[3
]}

机构：

[1] Univ Complutense Madrid, Fac Quim, Unidad Asociada CSIC, Grp Lactamas & Heterociclos Bioact,Dept Quim Org, E-28040 Madrid, Spain

[2] CSIC, IQOG, E-28006 Madrid, Spain

[3] Univ Complutense, Fac Quim, CAI Difracc Rayos 10, E-28040 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 16期

关键词：

MULTICOMPONENT REACTIONS; CLICK CHEMISTRY; AZETIDINE-2,3-DIONES; PEPTIDOMIMETICS; 1,2,3-TRIAZOLE; WATER;

D O I：

10.1021/jo301113g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Passerini (P-3CR) and Passerini-Smiles reactions were investigated in azetidine-2,3-diones, affording the corresponding 3,3-disubstituted-beta-lactams with complete diastereoselectivity in high yields. The study has been carried out using different isocyanides, carboxylic acids, and phenols showing the scope of both reactions. In addition, the regioselective synthesis of highly functionalized beta-lactam-triazole hybrids has been developed via a Passerini/CuAAC sequence. Interestingly, the use of dialkynes/diazides or trialkynes/triazides as linkers in the CuAAC step has allowed the synthesis of C-2 and C-3 symmetric beta-lactam-triazole hybrids, respectively.

引用

页码：6917 / 6928

页数：12

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