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dc.contributor.advisorReinecke, Manfred G.
dc.contributor.authorBrown, E. Sherwooden_US
dc.date.accessioned2019-10-11T15:10:02Z
dc.date.available2019-10-11T15:10:02Z
dc.date.created1989en_US
dc.date.issued1989en_US
dc.identifieraleph-516402en_US
dc.identifierMicrofilm Diss. 528en_US
dc.identifier.urihttps://repository.tcu.edu/handle/116099117/31800
dc.description.abstractThe 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.en_US
dc.format.extentvii, 159 leaves ; : illustrationsen_US
dc.format.mediumFormat: Printen_US
dc.language.isoengen_US
dc.relation.ispartofTexas Christian University dissertationen_US
dc.relation.ispartofAS38.B7683en_US
dc.subject.lcshAmino acids--Analysisen_US
dc.subject.lcshAminotriazinonesen_US
dc.subject.lcshCycloproparenoneen_US
dc.titleStudies of aminotriazinones: cycloproparenone precursors?en_US
dc.typeTexten_US
etd.degree.departmentDepartment of Chemistry
etd.degree.levelDoctoral
local.collegeCollege of Science and Engineering
local.departmentChemistry and Biochemistry
local.academicunitDepartment of Chemistry
dc.type.genreDissertation
local.subjectareaChemistry and Biochemistry
dc.identifier.callnumberMain Stacks: AS38 .B7683 (Regular Loan)
dc.identifier.callnumberSpecial Collections: AS38 .B7683 (Non-Circulating)
etd.degree.nameDoctor of Philosophy
etd.degree.grantorTexas Christian University


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