Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives

Abstract

The synthesis of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydropyrazolo[5,4-b] pyrimidino[5,4-e]pyridine-5-one (6) was achieved by two different one-pot multi-component synthesis (one-pot three-component and one-pot four component synthesis). Mono and dialkylation of 6 under different conditions gave compounds 7–11. The hydrazine 12 produced from reaction of 9 with N2H4 was subjected to reactions with some aromatic aldehydes, ethyl acetoacetate, acetyl acetone, ethyl cyanoacetate and triethyl orthoformate to give 13–17, respectively. Compound 12 upon reaction with CS2, nitrous acid, benzoin, chloroacetone and phenacyl bromide gave 18,20,21,22. Alkylation of 18 with ethyl iodide, ethyl chloroacetate and phenacyl bromide gave 19a–c. The antibacterial and antifungal activities of selected derivatives were evaluated.

Keywords

• one-pot reactions
• pyrazolo[5,4-b]pyrimidino[5,4-e]pyridines
• synthesis
• anti-microbial activity