dc.contributor.advisor | Reinecke, Manfred G. | |
dc.contributor.author | Brown, E. Sherwood | en_US |
dc.date.accessioned | 2019-10-11T15:10:02Z | |
dc.date.available | 2019-10-11T15:10:02Z | |
dc.date.created | 1989 | en_US |
dc.date.issued | 1989 | en_US |
dc.identifier | aleph-516402 | en_US |
dc.identifier | Microfilm Diss. 528 | en_US |
dc.identifier.uri | https://repository.tcu.edu/handle/116099117/31800 | |
dc.description.abstract | The photolysis of 3-lithio ((p-tolysulfonyl)amino) -1,2,3-benzotriazin-4-(3H)-one 1 in methanol gave among other products, 2-TsNHNHC$\sb6$H$\sb4$CO$\sb2$Me and not the reported 2-MeOC$\sb6$H$\sb4$CONHNHTs, suggesting the intermediacy of an azetidinone/iminoketene 2 rather than a 1,4-dipole 3 in these systems. The photolysis of 1 in THF gave, in addition to products derived solely from the tosyl group, 3-tosyloxyindazole 4 rather than the expected 1-tosylindazolin-3-one 5 or 2-tosylindazolin-3-one 6, arising from 3 and 2 respectively. Evidence is presented that 5 and/or 6 are initially formed from 1 and then rearrange to 4 by photodetosylation/tosylation via indazolin-3-one, or possibly via a photo-Fries-like reaction. The formation of indazolinones from this reaction has implications regarding the intermediacy of benzocyclopropenone 7 during the photo-decomposition of 1. The oxidation of 3-aminothienotriazinones 8 gives a thiophene analog of 7 that exhibits the reactivity of an electron rich 1,3-bidentate pi system, reacting with electron-deficient carbonyl compounds, but not with electron-rich traps, to give lactones. During the preparation of 8 the reaction of methyl or ethyl 2-amino-4,5,6,7-tetrahydrobenzo (b) thiophene-3-carboxylate with hydrazine gave the corresponding pyrazolo (3.4-c) pyridazine via the expected 2-amino-4,5,6,7-tetrahydrobenzo (b) thiophene-3-carboxhydrazide. | |
dc.format.extent | vii, 159 leaves ; : illustrations | en_US |
dc.format.medium | Format: Print | en_US |
dc.language.iso | eng | en_US |
dc.relation.ispartof | Texas Christian University dissertation | en_US |
dc.relation.ispartof | AS38.B7683 | en_US |
dc.subject.lcsh | Amino acids--Analysis | en_US |
dc.subject.lcsh | Aminotriazinones | en_US |
dc.subject.lcsh | Cycloproparenone | en_US |
dc.title | Studies of aminotriazinones: cycloproparenone precursors? | en_US |
dc.type | Text | en_US |
etd.degree.department | Department of Chemistry | |
etd.degree.level | Doctoral | |
local.college | College of Science and Engineering | |
local.department | Chemistry and Biochemistry | |
local.academicunit | Department of Chemistry | |
dc.type.genre | Dissertation | |
local.subjectarea | Chemistry and Biochemistry | |
dc.identifier.callnumber | Main Stacks: AS38 .B7683 (Regular Loan) | |
dc.identifier.callnumber | Special Collections: AS38 .B7683 (Non-Circulating) | |
etd.degree.name | Doctor of Philosophy | |
etd.degree.grantor | Texas Christian University | |