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Molecules 2008, 13(7), 1501-1517; doi:10.3390/molecules13071501
Article

Synthesis and Antimicrobial Activity of Some New Pyrazole, Fused Pyrazolo[3,4-d]-pyrimidine and Pyrazolo[4,3-e][1,2,4]- triazolo[1,5-c]pyrimidine Derivatives

1,* , 2
,
3
 and
1
1 Department of Chemistry, Faculty of Applied Sciences, Al-Aqsa University, 76888 Gaza, Palestine 2 Department of Chemistry, Faculty of Science, Cairo University, Egypt 3 Department of Chemistry, University College for Women, Ain Shams University, Heliopolis, Cairo, Egypt
* Author to whom correspondence should be addressed.
Received: 4 May 2008 / Revised: 21 July 2008 / Accepted: 22 July 2008 / Published: 29 July 2008
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Abstract

Hydrazonyl bromides 2a,b reacted with active methylene compounds (dibenzoylmethane, acetylacetone, ethyl acetoacetate, phenacyl cyanide, acetoacetanilide, ethyl cyanoacetate, cyanoacetamide and malononitrile) to afford the corresponding 1,3,4,5- tetrasubstituted pyrazole derivatives 5-12a,b. Reaction of 12a,b with formamide, formic acid and triethyl orthoformate give the pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4- d]pyrimidin-4(3H)one and 5-ethoxymethylene-aminopyrazole-4-carbo-nitrile derivatives 13-15a,b, respectively. Compounds 15a,b reacted with benzhydrazide and hydrazine hydrate to afford pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine and [4-iminopyrazolo- [3,4-d]pyrimidin-5-yl]amine derivatives 16a,b and 17a,b. Reactions of compounds 17a,b with triethyl orthoformate and carbon disulfide give the corresponding pyrazolo[4,3-e]- [1,2,4]triazolo[1,5-c]pyrimidine derivatives 18a,b and 19a,b, respectively.
Keywords: Hydrazonyl bromides; pyrazolo[3; 4-d]pyrimidine; pyrazolo[4; 3-e][1; 2; 4]- triazolo[1; 5-c]pyrimidine; antimicrobial activity. Hydrazonyl bromides; pyrazolo[3; 4-d]pyrimidine; pyrazolo[4; 3-e][1; 2; 4]- triazolo[1; 5-c]pyrimidine; antimicrobial activity.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Abunada, N.M.; Hassaneen, H.M.; Kandile, N.G.; Miqdad, O.A. Synthesis and Antimicrobial Activity of Some New Pyrazole, Fused Pyrazolo[3,4-d]-pyrimidine and Pyrazolo[4,3-e][1,2,4]- triazolo[1,5-c]pyrimidine Derivatives. Molecules 2008, 13, 1501-1517.

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