Acidic task specific ionic liquids catalyzed Groebke-Blackburn-Bienaymé reaction in the synthesis of imidazo[2,1-b]thiazoles

• Grant number: 17/06628-2
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Effective date (Start): August 01, 2017
• Effective date (End): February 28, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Luiz Sidney Longo Junior
• Grantee: Nicolas Santos dos Anjos
• Host Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

Multicomponent reactions (MCRs) are highly atom-economic organic transformations defined as processes that involve more than two starting materials combining together to afford a single product in which all atoms of the starting materials (or at least most of them) are incorporated into its structure. Imidazo[1,2-a]pyridine is present in several compounds with important biological activities (i.e. antimicrobial, antifungal, anxiolytic (Alpidem) and hypnotic (Zolpidem). This scaffold is easily accessed via the Groebe-Blackburn-Bienaymé (GBB) multicomponent reaction between an isocyanide, an aldehyde and 2-aminopyridine (as well as related amines). So far, several different protocols for GBB multicomponent reaction have been published elsewhere, most of them employing acid catalysts and common solvents under reflux for prolonged reaction time. The main goal of this proposal relies on the study of Bronsted acidic task specific ionic liquids as catalysts the GBB reaction involving 2-aminothiazole, aldehydes and commercially available isocyanides, under conventional or microwave heating, to afford imidazo[2,1-b]thiazoles, a privileged scaffold for drug discovery. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

ANJOS, NICOLAS S.; CHAPINA, AGATA I.; SANTOS, ANA R.; LICENCE, PETER; LONGO, LUIZ S., JR.. Groebke-Blackburn-Bienayme Multicomponent Reaction Catalysed by Reusable Br phi nsted-Acidic Ionic Liquids. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2022, n. 40, p. 8-pg., 2022-10-01. (17/06628-2, 18/15038-7, 19/01314-5)

SANTOS, GABRIELA F. D.; ANJOS, NICOLAS S.; GIBELI, MIGUEL M.; SILVA, GUILHERME A.; FERNANDES, PAMELA C. S.; FIORENTINO, EVERTON S. C.; LONGO JR, LUIZ S.. A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating. Journal of the Brazilian Chemical Society, v. 31, n. 7, p. 1434-1444, JUL 2020. (19/01314-5, 15/11155-0, 17/06628-2)