Synthesis of some Heterocyclic compounds containing non-mixed and mixed Systems of Potential Biological Activity.

Abstract

The thesis includes three Parts : Part I & II: The Reactivity and uses of 6-iodo-2-(phenylamino)- 4H-benzo[d][1,3]oxazin-4-one in the synthesis of quinazolinones 1) 6-Iodo-2-(phenylamino)-4H-benzo[d][1,3]oxazin-4-one 4 was synthesized via the reaction of 5-iodo anthranilic acid 1 with phenyl isocyanate 2 followed by refluxing with acetic anhydride. I COOH NH2 + PhN=C=O Dioxane I COOH NHCONHPh N O I NHPh O Ac2O 1 3 4 2 Scheme 1 2) The benzoxazinone derivative 4 reacted with sodium azide , ethyl acetoacetate, ethyl cyanoacetate , malonitrile, hydrazine hydrate, hydrazine hydrate in presence of carbon disulphide and potassium hydroxide in boiling ethanol to give N-(6-Iodo-4-oxo-2-(phenylamino) quinazolin-3(4H)-yl)ben-zamide 5, N'-(6-Iodo-4-oxo-2 (phenylamino)- 2,4-dihydro-1H-benzo[d][1,3]-oxazin-2yl)benzohydra-zide 6, 1-(2-acetyl-4-iodophen-yl)-3-phenylurea 7, 3-Amino-6-iodo-2- (phenylamino)quinazolin-4(3-H)-one 8, 1-(4-iodo-2-(5-thioxo-4,5- dihydro-1,3,4-oxadiazol-2-yl)phenyl)-3-phenylurea 9 respectively. N O I NHPh O N N I NHPh O NH2 N2H4.H2O 4 8 I CO2H N N N N PhHN I N NH CONHPh O NaN3 AcOH/ 5 6 + I 7 RCH2COOEt R = COOEt, CN, CH3CO N HNH Ph O H3C O I NHCONHPh O N NH 9 NH2NH2.H2O CS2/alc.KOH S Scheme 2 Part III novel quinazolin-4(3H)-one derivatives were synthesized by the reaction of hydrazonoyl chlorides with each of 6-iodo-2- phenylamino-3H-quinazolin-4-one and 3-amino-6-iodo-2- phenylamino-3H-quinazolin-4-one: 3) Amino quinazolinone reacted with phenyl isothiocyanate, benzaldhyde and β-aroyl acrylic acid, acetic anhydride, carbon disulphide, cycloheptanone, sodium nitrite in presence of hydrochloric acid and hydrozonoyl chloride to afford 1-(6-iodo-4- oxo-2-(phenylamino) quinazolin-3(4H)-yl)-3-phenylthiourea 10, 3- (benzylideneamino)-6-iodo-2-(phenylamino)quinazolin-4(3H)-one 11, 2-(2-(4-chloro-3-methylphenyl)-2-oxoethylidene)-8-iodo-4-phenyl- 1H-[1,2,4]triaz-ino(3,2-b)quinazoline-3,10(2H,4H)-dione 13, N- (6-iodo-4-oxo-2-(phenylamino)quinazolin-3(4H)-yl)acetamide 14, 7- iodo-3-phenyl-2-thioxo-2,3-dihydro-[1,2,4]triazolo[5,1-b]quinazolin9( 1H)one 15 , 3,4-cycloheptanopyrazole derivative 16, 3-((2- hydroxynaphthalen-1-yl)diazenyl)-6-iodo-2-(phenylamino)- quinazolin-4(3H)-one 17 and quinazolin-4(3H)-one derivatives 19 respectively.