Issue 8, 2018

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
13 Dec 2017
Accepted
18 Jan 2018
First published
19 Jan 2018

Org. Biomol. Chem., 2018,16, 1242-1246

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

O. Van der Poorten, R. Van Den Hauwe, K. Hollanders, B. U. W. Maes, D. Tourwé, M. Jida and S. Ballet, Org. Biomol. Chem., 2018, 16, 1242 DOI: 10.1039/C7OB03094K

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