The starting compound 4-amino-3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazole-5-carboxamide (1), that has been previously synthesized according to the literature procedure, underwent a reaction with the anhydride of phthalic acid either in AcOH or DMF to give isoindolinylpyrazole-5-carboxamide 3 and pyrazolothien-opyrimidoisoindoledione 4, respectively. Also, it was subjected to react with diethylmalonate followed by hydrazinolysis by hydrazine hydrate to yield the pyrazolothienopyrimidinyl acetohydrazide 5. The carbohydrazide derivative 5 was used as a key intermediate for the preparation of other new heterocyclic systems containing pyrazolylacetyl pyrazolothienopyrimidines and pyrazolothienopyrimidotriazepine compounds 6–11. The structures of these new heterocycles have been characterized by using analytical and spectroscopic analyses (IR, 1H-NMR, 13C-NMR and MS). Some derivatives of the synthesized compounds exhibited remarkable antibacterial and antifungal activities against many bacterial and fungal strains.

The starting compound 4-amino-3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazole-5-carboxamide (1), that has been previously synthesized according to the literature procedure, underwent a reaction with the anhydride of phthalic acid either in AcOH or DMF to give isoindolinylpyrazole-5-carboxamide 3 and pyrazolothien-opyrimidoisoindoledione 4, respectively. Also, it was subjected to react with diethylmalonate followed by hydrazinolysis by hydrazine hydrate to yield the pyrazolothienopyrimidinyl acetohydrazide 5. The carbohydrazide derivative 5 was used as a key intermediate for the preparation of other new heterocyclic systems containing pyrazolylacetyl pyrazolothienopyrimidines and pyrazolothienopyrimidotriazepine compounds 6–11. The structures of these new heterocycles have been characterized by using analytical and spectroscopic analyses (IR, 1H-NMR, 13C-NMR and MS). Some derivatives of the synthesized compounds exhibited remarkable antibacterial and antifungal activities against many bacterial and fungal strains.

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Reaction of 2-chloromethylquinazoline-4(3H)-one with some 3-cyanopyridine-2(1H)-thiones gave the
corresponding thioethers which upon treatment with appropriate base, underwent intramolecular ThorpeZeigler reaction affording the isomeric 3-amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]pyridines. In
contrast, the reaction of 2-chloromethylquinazoline-4(3H)-one with 3-cyanoquinoline-(1H)-thione gave 3-
amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]quinoline directly. Reaction of the resulting
aminothienopyridines/quinoline with some reagents namely; acetic anhydride, triethyl orthoformate and/ or
nitrous acid were carried out and their products were identified

Reaction of 2-chloromethylquinazoline-4(3H)-one with some 3-cyanopyridine-2(1H)-thiones gave the
corresponding thioethers which upon treatment with appropriate base, underwent intramolecular ThorpeZeigler reaction affording the isomeric 3-amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]pyridines. In
contrast, the reaction of 2-chloromethylquinazoline-4(3H)-one with 3-cyanoquinoline-(1H)-thione gave 3-
amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]quinoline directly. Reaction of the resulting
aminothienopyridines/quinoline with some reagents namely; acetic anhydride, triethyl orthoformate and/ or
nitrous acid were carried out and their products were identified

Reaction of 2-chloromethylquinazoline-4(3H)-one with some 3-cyanopyridine-2(1H)-thiones gave the
corresponding thioethers which upon treatment with appropriate base, underwent intramolecular ThorpeZeigler reaction affording the isomeric 3-amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]pyridines. In
contrast, the reaction of 2-chloromethylquinazoline-4(3H)-one with 3-cyanoquinoline-(1H)-thione gave 3-
amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]quinoline directly. Reaction of the resulting
aminothienopyridines/quinoline with some reagents namely; acetic anhydride, triethyl orthoformate and/ or
nitrous acid were carried out and their products were identified

Reaction of 2-chloromethylquinazoline-4(3H)-one with some 3-cyanopyridine-2(1H)-thiones gave the
corresponding thioethers which upon treatment with appropriate base, underwent intramolecular ThorpeZeigler reaction affording the isomeric 3-amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]pyridines. In
contrast, the reaction of 2-chloromethylquinazoline-4(3H)-one with 3-cyanoquinoline-(1H)-thione gave 3-
amino-2-(3,4-dihydro-4-oxo-2-quinazolinyl)thieno[2,3-b]quinoline directly. Reaction of the resulting
aminothienopyridines/quinoline with some reagents namely; acetic anhydride, triethyl orthoformate and/ or
nitrous acid were carried out and their products were identified

Abstract
A green, rapid, and efficient methodology is developed for the synthesis of
1-phenyl-3,5-pyrazolidinedione (3) by the reaction of malonic acid with phenyl
hydrazine in the presence of phosphorous oxychloride under solvent-free conditions.
The later compound 3 was used as a versatile precursor for green synthesis
of chalcone derivatives (4a-h) and spiroheterocyclic compounds (5a-h)
with good to excellent isolated yields. The chemical structures of the synthesized
compounds were elucidated on the basis of elemental and spectral
analyses.