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

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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

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Publication details

The article was received on 13 Dec 2017, accepted on 18 Jan 2018 and first published on 19 Jan 2018


Article type: Communication
DOI: 10.1039/C7OB03094K
Citation: Org. Biomol. Chem., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C7OB03094K

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