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Synthesis, Reactions and Characterization of 1,1’-(1,4-Phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(ethan-1-one)

Synthesis, Reactions and Characterization of 1,1’-(1,4-Phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(ethan-1-one)
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摘要 Reaction of 4,4’-(1,4-phenylene)bis(5-acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile) (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 af-forded the 1,1’-(1,4-phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(e-than-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. Reaction of 4,4’-(1,4-phenylene)bis(5-acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile) (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 af-forded the 1,1’-(1,4-phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(e-than-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.
作者 Ahmed A. M. Elreedy Hameed M. Alkubaisi Fawzy A. Attaby Ahmed A. M. Elreedy;Hameed M. Alkubaisi;Fawzy A. Attaby(Basic-Applied Science Department, Faculty of Oral and Dental Medicine, Nahda University, Beni-Suef, Egypt;College of Science for Women, Baghdad University, Baghdad, Iraq;Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt)
出处 《International Journal of Organic Chemistry》 CAS 2016年第1期65-76,共12页 有机化学国际期刊(英文)
关键词 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(ethan-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 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(ethan-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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