The Synthesis of 2-quinazolinones and Homologues


A brief historical perspective of quinazolines is given, as well as a review of the various synthetic routes reported in the preparation of these compounds. A more detailed literature survey of the procedures involved in the synthesis of 2-quinazolinones, and 4-quinazolinones' is described. In addition their chemical and biological activities are briefly reviewed. The synthesis of new 2(1H)-quinazolinones, and 2(1H)-quinazolinethiones, by two different methods is discussed. These include a novel synthesis involving the condensation of alkoxyphenylureas with a variety of acyl chlorides in polyphosphoric acid. Cyclodehydration = of N-acyl-N'-alkoxyphenylureas, and the corresponding thioureas in polyphosphoric acid, affords another convenient route toward the preparation of these compounds. The acylated ureas were prepared by acylation of N-alkoxyphenylureas with variously substituted acyl chlorides in benzene. While the acylated thioureas were obtained by reacting certain substituted aromatic amines with p-chlorobenzoyl isothiocyanate in acetone. Attempted preparations of new tricyclic derivatives of 2-quinazolinones, such as pyrrolo[3,2,1-ij])quinazolin-2-ones, pyrrolo[3,2,1-ij]quinazolin-2-thiones, and pyrido[3,2,1-ij]quinazolin-2-ones, using a variety of solvents and cyclising agents, are described. A brief discussion is presented for the preparation of some of their homologues. These include N-alkyl derivatives of 1,2,3,4-tetrahydrocarbazole, and 5,6-dihydrobenzo[a] carbazole. The latter was subjected to periodate oxidation to afford the expanded 9-membered ring 5-alkyl-11,12-dihydro-dibenz-{[b,g]azonin-6,13-dione.

Divisions: College of Health & Life Sciences > Aston Pharmacy School
Additional Information: Copyright © Mousa Ibrahim Jaeda, 1985. Mousa Ibrahim Jaeda asserts his moral right to be identified as the author of this thesis. This copy of the thesis has been supplied on condition that anyone who consults it is understood to recognise that its copyright rests with its author and that no quotation from the thesis and no information derived from it may be published without appropriate permission or acknowledgement. If you have discovered material in Aston Publications Explorer which is unlawful e.g. breaches copyright, (either yours or that of a third party) or any other law, including but not limited to those relating to patent, trademark, confidentiality, data protection, obscenity, defamation, libel, then please read our Takedown Policy and contact the service immediately.
Institution: Aston University
Uncontrolled Keywords: Acyl ureas,2(1H)-quinazolinone,2(1H)-quinazolinethione,Anti-inflammatory,Dibenzazoninedione
Last Modified: 28 Jun 2024 07:25
Date Deposited: 24 Jan 2011 14:13
Completed Date: 1985-09
Authors: Jaeda, Mousa Ibrahim

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