New 2,3-disubstituted quinazolin-4(3H)-ones from 2-undecyl-3,1-benz-oxazin-4-one

Authors: Mahmoud, Mahmoud R.; El-Bordany, Eman A.A.; Hassan, Naglaa F.; El-Azm, Fatma S.M. Abu

Source: Journal of Chemical Research, Volume 2007, Number 9, September 2007 , pp. 541-544(4)

Publisher: Science Reviews 2000 Ltd

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Abstract:

2-undecyl-4H-3,1-benzoxazin-4-one (2) was prepared and reacted with primary and secondary amines affording compounds 3-7, while with hydrazine hydrate it gave the quinazolinone derivative 8. The reaction of 8 with 3,4,5-trimethoxybenzaldehyde followed by thioglycollic acid yielded 9 and 10, respectively. Acylation of 8 using cinnamoyl chloride gave 11. Furthermore, treatment of 2 with hydrazine derivatives provided 12 and 13. Fusion of 2 with ammonium acetate gave the quinazolinone derivative 14 which upon treatment with ethyl chloroacetate yielded the ester 15. The hydrazide 17 was obtained from hydrazinolysis of the ester 15.

Keywords: QUINAZOLINONES, 3,1-BENZOXAZINONES

Document Type: Research article

DOI: 10.3184/030823407X248315