Thiourea as Bifunctional Hydrogen Bond Donor and Brønsted Base Catalyst for Green One-Pot Synthesis of 2-Aryl/Heteroaryl/Styryl Benzothiazoles in the Aqueous Medium under Ultrasound Irradiation.

Abstract

A green organocatalysis cascade strategy using thiourea in catalytic amounts as both a hydrogen bond donor and a Brønsted base bifunctional catalyst was utilized to synthesize a series of 2-aryl/heteroaryl/styryl benzothiazole derivatives. This strategy involved an ultrasound-irradiated one-pot two-component reaction between substituted aldehydes and 2-amino thiophenols in an aqueous medium at 60 °C, using air as an oxidant. At the gram-scale, this protocol yielded 87% of the desired product, making it suitable for production at a larger scale. This green and mild protocol offers excellent yields, cost-effectiveness, atom economy, step economy, and a simple operation that does not require extra purification steps. Furthermore, the catalyst is easily recoverable and can be used for up to five cycles without a significant loss of any activity.