Abstract
A new series of 3N-substituted triazolo-[1,5-c]pyrimidine 7, 8 and 9 have been synthesized in good yields (78–91%) trough a facile method using substituted 2-amino-3-cyano-pyrans 1, 2-amino-3-cyano-4-methylfuran 2, 1-Phenyl-3-thiomethyl-5-aminopyrazole-4-carbonitrile 3 as building block and cyanoacetic acid hydrazide as reagent in one framework. The structure of the synthesized compounds was established on the basis of their mass, spectral data and DFT at B3LYP.Graphic
Highlights
Pyrano, furano and pyrazolopyrimidine are priviliged structures, which attracted considerable attention in the designing of biologically active molecules
A facile method has been attempted by incorporating triazole and pyrimidine rings with substituted 2-amino-3-cyano-pyrans 1, 2-amino-3-cyano-4-methylfuran 2, 1-Phenyl-3-thiomethyl-5-aminopyrazole-4-carbonitrile 3, as building block in one framework (Scheme 1)
The synthetic route of the triazolopyrimidines 7, 8, and 9 is outlined in the Schemes 2, 3 and 4. “2-Amino-3-cyano4-methylfuran 1, 2-amino-3-cyano-pyrans 2, 1-Phenyl-3-thiomethyl-5-aminopyrazole-4-carbonitrile 3” were selected as our primary starting material for this synthesis and were prepared by methods taken from the literature [21,22,23], the reactivity of the cyanoacetic acid hydrazone has been already reported by the present authors [24, 28]
Summary
Furano and pyrazolopyrimidine are priviliged structures, which attracted considerable attention in the designing of biologically active molecules. Pyranotriazolopyrimidine derivatives have attracted a great deal of interest due to their biological activities and their potential applications as pharmacological agents. Several derivatives of the pyranotriazolopyrimidine exhibit platelet anti-aggregating activity and local “inhibition of influenza, virus sialidase and mutagenic. Scheme 1 General reactions interest works on heterocyclic compounds related to (pyrano, furano and pyrzolo)pyrimidines [17, 18], we wish to report the synthesis of new pyranotriazolopyrimidine 7, furanotriazolopyrimidine 8 and pyrazolotriazolopyrimidine 9 in the hope of obtaining compounds of diverse biological activities. (TDDFT) extends the basic thoughts of ground-state density-functional theory (DFT) to the treatment of excitations or more general time-dependent phenomena [19, 20] The compounds were investigated theoretically by density functional theory DFT and time-dependant density functional theory TD-DFT. (TDDFT) extends the basic thoughts of ground-state density-functional theory (DFT) to the treatment of excitations or more general time-dependent phenomena [19, 20]
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