Functionalization and Heteroannulation of Quinazolone Nucleus-Synthesis, Structure Elucidation and Bioactivity Evaluation

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dc.contributor.authorRASOOL KHAN
dc.contributor.authorSupervisor By: Dr. Mohammad Arfan
dc.date.accessioned2026-10-06T03:44:45Z
dc.date.available2026-10-06T03:44:45Z
dc.date.issued2008
dc.description.abstractThe research work documented in this dissertation presents the synthesis and bioactivity evaluation of some quinazolin-4(3.H)-one based heterocyclic compounds. Part first is concerned with the synthesis and synthetic methods both reported and newly designed and developed, while the second part is about the bioassays evaluation of the synthesized quinazolin-4(3H)-ones. 2-Aryl -4H-3,1-benzoxazin-4-one and methyl-Nacylanthranilates were prepared as starting materials for further transformations into a series of various 2,3-disubstituted quinazolin-4(3H)-ones. Keeping in view the extensive applications of 2-aryl -4H-3,1-benzoxazin-4-one as precursor in the quinazolin-4(3H)-ones chemistry, a new, cheaper andfacile one-pot method for the synthesis of 2-aryl -4H-3,1-benzoxazin-4-one was developed making use of readily available substituted benzoic acids. A faster and high- yielding microwaveassisted, solvent free method was also developed for the synthesis of methyl-2- [(trifluoroacetyl) amino] benzoate. Both the 2-aryl -4H-3,1-benzoxazin-4-one and methyl-N-acylanthranilates synthesized were then utilized for the synthesis of 3-amino, 2-alkyl/aryl quinazolin- 4(3H)-ones and 2,3-disubstituted quinazolin-4(3H)-ones. Consequently, a series of fifteen (19-33) 3-amino- 2-alkyl/aryl substituted quinazolin-4(3H)-ones anda series of twenty seven (46-62) 2,3-disubstituted quinazolin-4(3 H)-ones were synthesized. The necessity of development of new, cheaper and faster methods was realised and as a result, a simpler and less tedious three component one-pot method for the synthesis of ten ( 22-31) 3-amino, 2-aryl quinazolin-4(3H)-ones was developed starting from the available substituted benzoic acid. As a consequenceof the effect of substituents on the reactivity of 2-aryl -4H-3,1- benzoxazin-4-ones, three structurally novel quinazolin-4(3H)-ones (34-36) were synthesized from substituted 2-phenyl-4H-3,1-benzoxazin-4-ones. It was found that phenyl group substituted at position 2 failed to give any product. Reasons for the observed effect onthe reactivity are proposed. Keepingin view the importance of the nature and position of substituents in drug discovery, a series of (37-62) 2, 3-disubstituted quinazolin-4(3H)-ones were synthesized employing three different methods. The effect of substituents on the reactivity and the
dc.identifier.urihttp://repository.uop.edu.pk/123456789/635
dc.language.isoen
dc.publisherINSTITUTE OF CHEMICAL SCIENCES
dc.relation.ispartofseries100073
dc.titleFunctionalization and Heteroannulation of Quinazolone Nucleus-Synthesis, Structure Elucidation and Bioactivity Evaluation
dc.typeThesis
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