Pyridazine Derivative and Related Compound, Part 18:¹Pyridazino [3′,4′:3,4]pyrazolo [5,1-c]-1,2,4-triazine-3-carboxylic Acid: Synthesis, Reactions, and Antimicrobial Activity

Abstract

A series of 3-substituted pyridazino[3′,4′:3,4]pyrazolo[5,1-c]-1,2,4-triazens have been synthesized starting from the 3-carboxylic acid derivative 2. The reaction of the acid chloride 3 with amines gave the corresponding anilides 4. The reaction of 2 with ethyl chloroformate and sodium azide in the presence of triethyl amine gave the carbonyl azide 5, which underwent a Curtius rearrangement in boiling ethanol to afford the carbamate 6, which converted to the 3-amino derivative 7 upon alkaline hydrolysis, and the reaction with acid chloride resulted in N-substituted products 9. On other hand, the reaction of the carboxylic acid 2 with POCl₃ and thiosemicarbazide afforded 2-amino-1,3,4-thiadiazole derivative 13. The condensation of 13 with aldehydes furnished 14 in a good yield. The products were screened for their antimicrobial activity against six microorganisms.

Keywords:

• Keywords
• Antimicrobial
• 3-subsitituted pyridazinopyrazolotriazines

Acknowledgments

The authors acknowledge the help of Dr. Gamal El-Sherbeny, Department of Microbiology, Faculty of Science, El-Azhar University, Cairo, for carrying out the antimicrobial activity.