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Microwave Assisted Synthesis and Characterization of Some Quinazolinone Based Condensed Heterocycles

V. Niraimathi, A. Jerad Suresh, Ajitha Das Aruna and R. Uma Maheswari

Solvent free synthetic approach towards greener chemistry was followed by microwave irradiation technique. Novel series of oxazole/thiazole ring fused amino quinazolinones were synthesized and characterized. Quinazolinones represent a useful template for their wide array of pharmacological properties. Microwave irradiation technique contributed to better yield of product with shorter reaction time and minimal byproducts. Anthranilic acid (1) was subjected to react with 4-chloro -3-nitro benzoylchloride (2) leading the production of 2-(4-chloro-3-nitrophenyl)- 4H-3, 1 benzoxazin- 4-one (3). Subsequently (3) was refluxed with 80% hydrazine hydrate (4) using pyridine to yield 3-amino-2-(4- chloro-3-nitrophenyl) quinazolin -4(3H) one (5). 2-Chloro-N-(2-(4-chloro-3-nitrophenyl)-4- oxoquinazolin-3(4H)-yl)acetamide (7) was synthesized by stirring and refluxing (5) with chloroacetylchloride (6). The title compounds 3-[(2-substituted -1, 3 oxazole/ thiazole ) amino] 2-(3- chloro-4-nitrophenyl)quinazolinone-(9a - 9f) were synthesized by reacting (7) with different urea derivatives (8a-8f) in presence of ethanol under microwave irradiation technique. All synthesized compounds were characterized by IR, NMR and MS spectral data.