Abstract
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.
Highlights
The chemistry of heterocyclic compounds has attracted attention in recent times due to its increasing importance in the field of pharmaceuticals and industries
The biological importance of both bis-compounds [18]-[21] and 2-thioxopyridine-3-carbonitriles [22]-[24] as well as the conjunction to our previous work [25]-[33] stimulated our interest to synthesize several derivatives of these ring systems that are required for several chemical transformations and medicinal chemistry programs
An unequivocal support for the structure of compound 1 [20] came from the series of reactions concerning the presence and synthetic potentiality of NH, C=S and CN functional groups in 4,4’-(1,4-phenylene)bis(5-acetyl6-methyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile) 1 and this stimulated our interest to use it as the good starting material for the present study aiming for further chemical transformation required for our medicinal chemistry programs
Summary
The chemistry of heterocyclic compounds has attracted attention in recent times due to its increasing importance in the field of pharmaceuticals and industries. The synthesis of bis-heterocyclic compounds exhibits various biological activities [1]-[8] including antibacterial, fungicidal, tuberculostatic, antiamoebic, and plant growth regulative properties. Bis-compounds have received great attention [9] [10] for being model compounds for main chain polymers [11]-[16] and because many biologically active natural and synthetic products have molecular symmetry [17]. The biological importance of both bis-compounds [18]-[21] and 2-thioxopyridine-3-carbonitriles [22]-[24] as well as the conjunction to our previous work [25]-[33] stimulated our interest to synthesize several derivatives of these ring systems that are required for several chemical transformations and medicinal chemistry programs
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