Affiliation:
1. Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro
Abstract
A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for α-monohalogenation of β-keto esters in aqueous medium, which in the presence of thiourea and DABCO produced the corresponding 2-aminothiazoles in up to 87% yield. Extension of the reaction to thioacetamide and o-phenylenediamine led to 2-methylthiazole and quinoxalines, respectively. This approach enables telescoping of the two steps into a single process.
Subject
Organic Chemistry,Catalysis
Cited by
25 articles.
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1. Trihaloisocyanuric Acids: Useful Reagents for Halogenation Reactions and
Heterocyclic Scaffold Construction;Current Organic Chemistry;2024-07
2. Microwave-Assisted One-Pot Telescoped Synthesis of 2-Amino-1,3-thiazoles, Selenazoles, Imidazo[1,2-a]pyridines, and Other Heterocycles from Alcohols;The Journal of Organic Chemistry;2024-03-18
3. Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles;ChemistrySelect;2023-12-13
4. An eco‐friendly synthesis of 5‐aminotetrazoles using trichloroisocyanuric acid as desulfurization agent of thioureas;Journal of Heterocyclic Chemistry;2023-05-15
5. Tribromoisocyanuric acid as an alternative oxidant in the synthesis of 2-amino-1,3,4-oxadiazoles from 1-acylthiosemicarbazides;Tetrahedron Letters;2023-05