Thiazoles/selenazoles/oxazoles are ubiquitous pharmacophores present in several biologically active and commercially important molecules. For example, thiazolium ring has found its utility in various drugs including antibacterial, antiprion, anti-inflammatory, fungicides, and anti-HIV agents. Selenazofurin (1,3-selenazole core), a selenium analogue of antitumor agent tiazofurin (1,3-thiazole core), is widely used as an antibiotic and for tumor stasis. Similarly, oxazoles derivatives have found versatile applications in pharmaceutical and textile industry. Herein, we report the unique and remarkably efficient procedure for the synthesis of thiazoles/selenazoles/oxazoles. We have utilized a Syrris flow chemistry microfluidic reactor to perform these reactions in a much more facile manner with a cleaner reaction profile, high yields, quick scalability with minimum optimization needed for bulk reaction and without the need of any catalyst. We are able to accelerate the process by increasing temperature and pressure to achieve 95-100% yield with short residence time (minutes) in the microfluidic reactor as compared to 1-12 hour traditional cyclocondensation reactions. This green chemistry approach can be utilized to make important bioactive molecules/intermediates in a continuous and safe manner.

Facile cyclocondensation in a microfluidic reactor for continuous synthesis of thiazoles/selenazoles/oxazoles

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.