Green Synthesis of Novel [1,3,4]Thiadiazolo[3,2-a]Pyrimidines via Three-Component Reaction of 5-Amino-1,3,4-Thiadiazole-2-Thiol, Aromatic Aldehydes, and Meldrum’s Acid

Abstract

A novel and highly efficient synthetic route to [1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives from 5-amino-1,3,4-thiadiazole-2-thiol, various aromatic aldehydes, and Meldrum’s acid in the presence of acetic acid in dry ethanol has been reported. We designed the three-component reaction with the incorporation of Knoevenagel condensation followed by an intermolecular nucleophilic addition reaction in one pot under mild conditions. The structural diversities of these synthesized compounds have been confirmed spectroscopically, by IR, ¹H-, and ¹³C NMR, and elemental analysis, which agree with the proposed structures.

Graphical Abstract

Keywords:

• 5-amino-1,3,4-thiadiazole-2-thiol
• [1,3,4]Thiadiazolo[3,2-a]pyrimidines
• aromatic aldehydes
• three-component reaction
• Meldrum’s acid

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The authors would like to thank the Office of Graduate Studies of Vali-e-Asr University of Rafsanjan, for their partial financial support and cooperation. This research was supported by the Iran National Science Foundation (INSF) under grant number 99018081.