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Vol. 30 No. 8 (2018): Vol 30 Issue 8

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Synthesis of New Oxadiazole, Triazole and Oxazepine Derivatives of Quinazoline Moiety

https://doi.org/10.14233/ajchem.2018.21277
Fadhel Omran Essa*
Department of Chemistry, College of Basic Education, University of Babylon, Hilla, Iraq *Corresponding author: E-mail: fathel_omran61@yahoo.com
Kadhum J.K. Al-Hamdani
Department of Chemistry, College of Basic Education, University of Babylon, Hilla, Iraq *Corresponding author: E-mail: fathel_omran61@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 8 (2018): Vol 30 Issue 8

Abstract

New 2-(4-oxo-2-phenylquinazolin-3(4H)-yl)-3-phenyl propanoic acid derivatives have been prepared by reaction of 2-phenyl-4H-1,3-benzoxazin-4-one with phenylalanine. The reaction of compound 1 with thionyl chloride produced 2-[4-oxo-2-phenylquinazolin-3(4H)-yl]-3-phenylpropanoyl chloride (2). Condensation of compound 2 with hydrazine hydrate afforded 2-[4-oxo-2-phenylquinazolin-3(4H)-yl]-3-phenyl propane hydrazide (3). The reaction of compound 3 with carbon disulfide and potassium hydroxide yielded 3-[1-(5-mercapto-1,3,4-oxadiazol-2-yl)-2-phenylethyl]-2-phenylquinazolin-4(3H)-one (4). Teratment of compound 4 with hydrazine hydrate gave 3-[1-(5-mercapto-4H-1,2,4-triazol-3-yl)-2-phenylethyl]-2-phenylquinazolin-4(3H)-one (5). The reaction of compound 3 with phenyl isothiocyanate resulted in formation of 2-[2-(2-phenyl-4-oxoquinazolin-3(4H)-yl)-3-phenylpropanoyl]hydrazine carbothioamide (6). Treatment of compound 6 with aqueous sodium hydroxide solution produced 3-[1-(5-mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)-2-phenylethyl]2-phenylquinazolin-4(3H)-one (7). The azomethines 8a-d were synthesized from the reaction between the corresponding aldehydes and acid hydrazide 3. Moreover, N-(3-methyl-1,5-dioxobenzo[e][1,3]oxazepin-4(1H,3H,5H)-yl-2-(4-oxo-2-phenyl quinazoline-3(4H)-yl)acetamide 9a-d were synthesized from the cyclic condensation of imines with phthalic anhydride. The structure of novel synthesized compounds were suggested from IR, 1H NMR and and 13C NMR spectral studies.

Keywords

Oxazines Oxazepines Oxadiazoles Triazoles Phenylquinazolines.
Omran Essa*, F., & J.K. Al-Hamdani, K. (2018). Synthesis of New Oxadiazole, Triazole and Oxazepine Derivatives of Quinazoline Moiety. Asian Journal of Chemistry, 30(8), 1706–1710. https://doi.org/10.14233/ajchem.2018.21277
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