The synthesis and reactions of sulphur analogues of deoxyvasicinone

The synthesis of the thiazolo -, thiazin - and thiazepino- quinazolinones (A)-(C) was achieved, by the condensation of anthranilic acid with appropriate sulphur containing lactams, in the presence of phosphoryl chloride. The quinazolinones (A) and (B) were shown to react (at the methylene group alpha to the carbon-nitrogen double bond) with a variety of electrophiles at elevated temperatures. Compound (C) was found to be inert to electrophiles under the same reaction conditions.<br/><br/>The ability of the heterocycles (A)-(C)to react with heterocumulenes, following deprotonation with sodium hydride in DMSO, was demonstrated. Reaction of the anion derived from (B) with alkylating agents, Michael acceptors and activated halopyridines afforded novel substituted derivatives. The oxidation, Pummerer rearrangement and deacetylation of (A)-(C) was accomplished to yield analogues which were similar in structure to the biologically active compound vasicinone. A series of C-ring substituted analogues of (A) were prepared and the sulphoxides derived from these compounds subjected to Pummerer rearrangement.<br/><br/>(A) and (B) were oxidatively ring opened on treatment with excess peracetic acid, whilst under similar reaction conditions (C) gave a sulphone. Investigations in to the reduction of substituted derivatives of (B) led to the novel tetracyclic compound (D).

Name dc:type.qualificationname

PhD

Level dc:type.qualificationlevel

Doctoral Thesis

Year dc:date.issued

1989

Author dc:creator

• Norrie, Robert

Language dc:language

eng

Identifier

oai:rke.abertay.ac.uk:studenttheses/90b18814-909e-42fd-9ff5-60696063c24d

OAI identifier oai:identifier

oai:rke.abertay.ac.uk:studenttheses/90b18814-909e-42fd-9ff5-60696063c24d