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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 3amino-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.

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Synthesis and characterization of new quinazolinylmethylsulfanylpyridines, quinazolinylthieno[2,3-b]pyridines and pyrido[3",2":4',5'] thieno[3',2':4,5]pyrimido[6,1-b]quinazolines