A simple, facile and greener route to thiazolo[3,2-c]pyrimidinones in semi-aqueous medium and their antibacterial properties

Abstract

By using easily accessible heterocyclic enamines, acetaldehyde (or formaldehyde) and primary amines as suitable precursors, a water-assisted three-component synthesis of new 3-oxothiazolo[3,2-c]pyridimines has been efficiently achieved in mild and semi-aqueous medium. All the cyclization reactions under optimized and catalyst-free conditions furnish the target compounds in 40–100% yields. Although cyclizations with arylamines in the presence of formaldehyde yield moderate to good yields, certain cyclizations involving aryl amines in the presence of acetaldehyde do not result in any product formation. Structural characterization of all the products were performed by means of FT-IR,¹H and ¹³C NMR and HRMS analyses. Besides, some of the products demonstrated bacteriostatic effects in the antibacterial study conducted against S. aureus and S. epidermidis bacteria.

GRAPHICAL ABSTRACT

Keywords:

• 3-oxothiazolo[3,2-c]pyrimidine
• heterocyclic enamine
• 3-CR
• multicomponent
• antimicrobial

Disclosure statement

No potential conflict of interest was reported by the author(s).

Correction Statement

This article has been corrected with minor changes. These changes do not impact the academic content of the article.

Additional information

Funding

Bolu Abant Izzet Baysal University, Directorate of Research Projects Commission [grant no. 2015.03.03.931 and 2016.03.03.1071] are greatly acknowledged for financial supports.