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Synthesis, Reactions and Characterization of 1,1'-(1,4-Phenylenebis(3-Amino-6-Methyl-1 H-Pyrazolo[3,4-b]pyridine-4,5-Diyl))bis(eth An-1-One)


Affiliations
1 Basic-Applied Science Department, Nahda University, Beni-Suef, Egypt
2 College of Science for Women, Baghdad University, Baghdad, Iraq
3 Chemistry Department, Cairo University, Giza, Egypt
 

Reaction of 4,4'-(1,4-phenylene)bis(5-acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carboni-trile) (1) with methyl iodide afforded the 4,4'-(1,4-phenylene)bis(5-acetyl-6-methyl-2-(methylthio)nicotinonitrile) (2). The reaction of 2 with hydrazine hydrate followed by diazotization reaction afforded the 1,1'-(1,4-phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(ethan- 1-one) (3) and 1,1'-(1,4-phenylenebis(3-(chlorodiazenyl)-6-methyl-1H-pyrazolo[3,4-b]- pyridine- 4,5-diyl))bis(ethan-1-one) (4) respectively. On the other hand, reaction of 4 with malononitrile, 2-cyanoethanethioamide, ethyl acetoacetate, acetyl acetone, ethyl benzoylacetate, diethylmalonate, ethyl cyanoacetate and phenacylbromide aiming to build up pyrazolotriazine or pyrazole ring on the ring system of 4. Structures of all newly synthesized heterocyclic compounds in the present study were confirmed by considering the data of IR, 1H NMR, mass spectra as well as that of elemental analyses.

Keywords

Bis-1,2-Dihydropyridine-3-Carbonitrile, Bis-Nicotinonitrile, 1,1’-(1,4-Phenyl-Enebis(3-(Chlorodiazenyl)-6-Methyl-1h-Pyrazolo[3,4-b]Pyri-Dine-4,5-Diyl))bis(et Han-1-One), Bis-Dihydropyrido[2’,3’:3,4]Pyrazolo[5,1-C][1,2,4]Triazine-3-Carboxylate, Bis-1h-Pyrazolo[3,4-b]Pyridine.
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  • Synthesis, Reactions and Characterization of 1,1'-(1,4-Phenylenebis(3-Amino-6-Methyl-1 H-Pyrazolo[3,4-b]pyridine-4,5-Diyl))bis(eth An-1-One)

Abstract Views: 95  |  PDF Views: 0

Authors

Ahmed A. M. Elreedy
Basic-Applied Science Department, Nahda University, Beni-Suef, Egypt
Hameed M. Alkubaisi
College of Science for Women, Baghdad University, Baghdad, Iraq
Fawzy A. Attaby
Chemistry Department, Cairo University, Giza, Egypt

Abstract


Reaction of 4,4'-(1,4-phenylene)bis(5-acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carboni-trile) (1) with methyl iodide afforded the 4,4'-(1,4-phenylene)bis(5-acetyl-6-methyl-2-(methylthio)nicotinonitrile) (2). The reaction of 2 with hydrazine hydrate followed by diazotization reaction afforded the 1,1'-(1,4-phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(ethan- 1-one) (3) and 1,1'-(1,4-phenylenebis(3-(chlorodiazenyl)-6-methyl-1H-pyrazolo[3,4-b]- pyridine- 4,5-diyl))bis(ethan-1-one) (4) respectively. On the other hand, reaction of 4 with malononitrile, 2-cyanoethanethioamide, ethyl acetoacetate, acetyl acetone, ethyl benzoylacetate, diethylmalonate, ethyl cyanoacetate and phenacylbromide aiming to build up pyrazolotriazine or pyrazole ring on the ring system of 4. Structures of all newly synthesized heterocyclic compounds in the present study were confirmed by considering the data of IR, 1H NMR, mass spectra as well as that of elemental analyses.

Keywords


Bis-1,2-Dihydropyridine-3-Carbonitrile, Bis-Nicotinonitrile, 1,1’-(1,4-Phenyl-Enebis(3-(Chlorodiazenyl)-6-Methyl-1h-Pyrazolo[3,4-b]Pyri-Dine-4,5-Diyl))bis(et Han-1-One), Bis-Dihydropyrido[2’,3’:3,4]Pyrazolo[5,1-C][1,2,4]Triazine-3-Carboxylate, Bis-1h-Pyrazolo[3,4-b]Pyridine.