Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl⋅6H2O deep eutectic solvent

Mehri Moeini Korbekandi; Iraj Mohammadpoor-Baltork; Majid Moghadam; Shahram Tangestaninejad; Valiollah Mirkhani; Behrouz Notash

doi:10.1038/s41598-024-52017-3

Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl⋅6H₂O deep eutectic solvent

Sci Rep. 2024 Jan 16;14(1):1451. doi: 10.1038/s41598-024-52017-3.

Authors

Mehri Moeini Korbekandi¹, Iraj Mohammadpoor-Baltork², Majid Moghadam¹, Shahram Tangestaninejad¹, Valiollah Mirkhani¹, Behrouz Notash³

Affiliations

¹ Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan, 81746-73441, Iran.
² Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan, 81746-73441, Iran. imbaltork@sci.ui.ac.ir.
³ Department of Inorganic Chemistry, Shahid Beheshti University, Tehran, Iran.

Abstract

In this research, a new Lewis acid-based deep eutectic solvent (LA-DES) was synthesized using diphenhydramine hydrochloride and CoCl₂·6H₂O, (2[HDPH]:CoCl₄^2-), and identified by FT-IR and ¹HNMR techniques. The physicochemical properties of this LA-DES, such as thermal behavior, thermal stability, and solubility in common solvents were also investigated. The catalytic ability of 2[HDPH]:CoCl₄^2- was ascertained in the efficient synthesis of a novel array of thiadiazolo[2,3-b]quinazolin-6-one scaffolds via a one-pot three-component reaction of dimedone/1,3-cyclohexanedione, aldehydes, and 5-aryl-1,3,4-thiadiazol-2-amines/3-(5-amino-1,3,4-thiadiazol-2-yl)-2H-chromen-2-one under solvent-free conditions. This catalyst was also successfully utilized for the synthesis of mono- and bis-thiadiazolo[2,3-b]quinazolin-6-ones from dialdehydes or bis-1,3,4-thiadiazol-2-amine. The simplicity of enforcement, short reaction time, avoidance of toxic organic solvents, scalability of the synthesis procedure, excellent atom economy, high reaction mass efficiency, and low E-factor are other outstanding advantages of this newly developed method. Furthermore, due to the convenient recovery and reuse of LA-DES, this protocol is economically justified and environmentally friendly.