Catalyst-Free Synthesis of Polysubstituted 5-Acylamino-1,3-Thiazoles via Hantzsch Cyclization of α-Chloroglycinates

Mara Tomassetti; Gabriele Lupidi; Pamela Piermattei; Federico V Rossi; Samuele Lillini; Gianluca Bianchini; Andrea Aramini; Marco A Ciufolini; Enrico Marcantoni

doi:10.3390/molecules24213846

Catalyst-Free Synthesis of Polysubstituted 5-Acylamino-1,3-Thiazoles via Hantzsch Cyclization of α-Chloroglycinates

Molecules. 2019 Oct 25;24(21):3846. doi: 10.3390/molecules24213846.

Authors

Mara Tomassetti¹, Gabriele Lupidi², Pamela Piermattei², Federico V Rossi², Samuele Lillini¹, Gianluca Bianchini³, Andrea Aramini^{1

3}, Marco A Ciufolini⁴, Enrico Marcantoni²

Affiliations

¹ Dompé Farmaceutici S.p.A., Via Pietro Castellino, Napoli 80131, Italy.
² School of Science and Technology, Chemistry Division, University of Camerino, Camerino 62032, Italy.
³ Dompé Farmaceutici S.p.A., Via Campo di Pile, L'Aquila 67100, Italy.
⁴ Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Abstract

A catalyst-free heterocyclization reaction of α-chloroglycinates with thiobenzamides or thioureas leading to 2,4-disubstituted-5-acylamino-1,3-thiazoles has been developed. The methodology provides straightforward access to valuable building blocks for pharmaceutically relevant compounds.

Keywords: 5-acylamino-1,3-thiazoles; Hantzsch reaction; α-chloroglycinates.

MeSH terms

Catalysis
Cyclization*
Molecular Structure*
Thiazoles / chemical synthesis*
Thiazoles / chemistry

Substances

Thiazoles