通过 Ugi-4CR-Ullmann 交叉偶联序列快速构建取代的 3-氨基-1,5-苯并硫氮杂卓-4(5H)-酮二肽支架。

Rapid construction of substituted 3-amino-1,5-benzothiazepin-4(5H)-one dipeptide scaffolds through an Ugi-4CR - Ullmann cross-coupling sequence.

机构信息

Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, B-1000 Brussels, Belgium.

出版信息

Org Biomol Chem. 2018 Feb 21;16(8):1242-1246. doi: 10.1039/c7ob03094k.

DOI:10.1039/c7ob03094k

PMID:29379930

Abstract

A 3-step methodology for the synthesis of 1,5-benzothiazepin-4(5H)-one dipeptidomimetics has been elaborated via an Ugi-4CR followed by a S-trityl deprotection and an intramolecular Cu(i)-catalyzed Ullmann condensation with moderate to good yields. In silico and NMR conformational studies showed that the lowest energy conformers stabilize γ- and β-turn structures.

摘要

已经详细阐述了通过 Ugi-4CR 反应、S-三苯甲基脱保护反应和分子内 Cu(i)-催化的Ullmann 缩合反应三步法合成 1,5-苯并硫氮杂卓-4(5H)-酮二肽类似物的方法，产率中等至良好。计算和 NMR 构象研究表明，最低能量构象稳定γ-和β-转角结构。