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Issue 13, 2018
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Synthesis of thioureido peptidomimetics employing alkyl azides and dithiocarbamates

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Abstract

An unprecedented approach for the assembly of thioureido peptidomimetics is developed employing alkyl azides and dithiocarbamates. Dithiocarbamates react with alkyl azides with the liberation of N2 and elemental sulfur thereby leading to thiourea in a traceless manner. Thioureido peptidomimetics are thus furnished in good yields with no epimerization. This process is mild, free from the use of a base, scalable and step economic. The practicability of this methodology has been highlighted by the synthesis of N,N′-orthogonally protected thioureido peptidomimetics.

Graphical abstract: Synthesis of thioureido peptidomimetics employing alkyl azides and dithiocarbamates

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Publication details

The article was received on 29 Jan 2018, accepted on 28 Feb 2018 and first published on 02 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00239H
Citation: Org. Biomol. Chem., 2018,16, 2258-2263
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    Synthesis of thioureido peptidomimetics employing alkyl azides and dithiocarbamates

    L. Roopesh Kumar, V. Panduranga, T. M. Vishwanatha, Shekharappa and Vommina. V. Sureshbabu, Org. Biomol. Chem., 2018, 16, 2258
    DOI: 10.1039/C8OB00239H

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