Molecules 2012, 17(12), 14464-14483; doi:10.3390/molecules171214464
Article

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

Talaat I. El-Emary* email and Shawkat A. Abd El-Mohsen
Department of Chemistry, Faculty of Science, Assiut University, Assiut 71516, Egypt
* Author to whom correspondence should be addressed.
Received: 24 October 2012; in revised form: 25 November 2012 / Accepted: 27 November 2012 / Published: 6 December 2012
(This article belongs to the Section Organic Synthesis)
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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

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MDPI and ACS Style

El-Emary, T.I.; El-Mohsen, S.A.A. 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. Molecules 2012, 17, 14464-14483.

AMA Style

El-Emary TI, El-Mohsen SAA. 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. Molecules. 2012; 17(12):14464-14483.

Chicago/Turabian Style

El-Emary, Talaat I.; El-Mohsen, Shawkat A.A. 2012. "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." Molecules 17, no. 12: 14464-14483.

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