Efficient one-pot synthesis of amino-benzotriazolodiazocinone scaffolds via catalyst-free tandem Ugi-Huisgen reactions

被引：13

作者：

Barlow, T. M. A. ^{[1
,2
]}

Jida, M. ^{[1
,2
]}

Guillemyn, A. K. ^{[1
,2
]}

Tourwe, D. ^{[1
,2
]}

Caveliers, V. ^{[3
]}

Ballet, S. ^{[1
,2
]}

机构：

[1] Vrije Univ Brussel, Dept Chem, Res Grp Organ Chem, Pleinlaan 2, B-1000 Brussels, Belgium

[2] Vrije Univ Brussel, Dept Bioengn Sci, Res Grp Organ Chem, Pleinlaan 2, B-1000 Brussels, Belgium

[3] Vrije Univ Brussel, In Vivo Cellular & Mol Imaging ICMI Lab, Laarbeeklaan 103, B-1090 Brussels, Belgium

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 20期

关键词：

BETA-TURN MIMICS; C-H AZIDATION; MULTICOMPONENT REACTIONS; BIOLOGICAL EVALUATION; OPIOID AGONIST; LACTAMIZATION; DERIVATIVES; ANTAGONISTS; ANILINES; DESIGN;

D O I：

10.1039/c6ob00438e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe a catalyst-free, one-pot procedure employing an Ugi-4CR between propargyl glycine, functionalised 2-azidoanilines, different isocyanides and aldehydes, followed by a thermal azide-alkyne Huisgen cycloaddition to generate a 14-member set of amino-benzotriazolodiazocine-bearing dipeptides with multiple points of diversification and high atom economy. These structures were derivatized by means of Suzuki-Miyaura cross-coupling reactions at two positions with good to excellent yields, leading to conformationally constrained tricyclic structures. In silico and NMR conformational analysis studies demonstrated that turn conformations are adopted by these structures.

引用

页码：4669 / 4677

页数：9

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