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dc.contributor.advisorMinter, David E.
dc.contributor.authorRe, Michael Angeloen_US
dc.description.abstractIsoquinoline-N-borane was used as an intermediate to synthesize 1-substituted and 1,4-disubstituted 1,2,3,4-tetrahydroisoquinolines. Organolithium reagents were added to C-1 to give enamine intermediate 1. Protonation of 1 led to 1-substituted tetrahydroisoquinolines; and addition of alkyl halides to 1 gave 1,4-disubstituted products. Electrophilic addition to C-4 was stereoselective in that the electrophile added selectively cis to the C-1 substituent. 1 was also shown to be an active hydride source. The adduct of sodium triethylborohydride and isoquinoline gave a boron-activated enamine 2 which was also a useful intermediate. Additions of alkyl halides to 2 led to 4,4-disubstituted tetrahydroisoquinolines. In the most useful procedure, aldehydes reacted with 2 in a three-step "one-pot" reaction sequence to give 4-substituted isoquinolines. Other aspects of the chemistry of intermediates 1 and 2 is described as well as the synthetic utility and limitations of this methodology.
dc.format.extentvii, 114 leaves, bound : illustrationsen_US
dc.format.mediumFormat: Printen_US
dc.relation.ispartofTexas Christian University dissertationen_US
dc.titleA new approach to the synthesis of substituted isoquinolinesen_US
dc.typeTexten_US of Chemistry
local.collegeCollege of Science and Engineering
local.departmentChemistry and Biochemistry
local.academicunitDepartment of Chemistry
local.subjectareaChemistry and Biochemistry
dc.identifier.callnumberMain Stacks: AS38 .R4 (Regular Loan)
dc.identifier.callnumberSpecial Collections: AS38 .R4 (Non-Circulating) of Philosophy Christian University

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