Abstract
Behaviour of dynamic 6,8-dibromo-2-methyl-4-(H)-3, 1-benzoxazin-4-one towards some nitrogen nucleophiles: Synthesis of newquinazolinoneswith anticipated biological activity
Author(s): H.M.F.Madkour, M.E.Azab, D.A.Mhanna, M.A.El-Hashash4(H)-3,1-Benzoxazin-4-one derivative 1 reactedwith ammoniumacetate and/ or formamide, hydrazine hydrate and ethanolamine to give pyrimidine derivatives 2-4. Treatment of 2 with P2S5 and ethyl chloroacetate produced thazine 5 and ester 7 which upon reaction with hydrazine furnished the hydrazide 8. The hydrazide 8 reacted with CS2/KOH at roomtemperature and/or reflux, benzoyl chloride, 2-chlorobenzoic acid/POCl3, and pchlorobenzaldehyde to afford pyrimidine derivatives 9, 11-14, respectively. On the other hand, when the aminopyrimidine derivative 3 reacted with pchlorobenzaldehyde, phthalimide and ethyl acetoacetate, it produces the quinazolinones 18-20, respectively. Furthermore, refluxing the 1,3-diketone 20 with hydrazine and benzylamine gave the pyrazole derivative 21, and the condensation product 22, respectively.All newsynthesized compounds were structurally confirmed by elemental analyses and spectroscopic data (IR, 1H-NMR and MS spectroscopy).
