dc.contributor.advisor | Minter, David E. | |
dc.contributor.author | Re, Michael Angelo | en_US |
dc.date.accessioned | 2019-10-11T15:10:02Z | |
dc.date.available | 2019-10-11T15:10:02Z | |
dc.date.created | 1987 | en_US |
dc.date.issued | 1987 | en_US |
dc.identifier | aleph-252086 | en_US |
dc.identifier.uri | https://repository.tcu.edu/handle/116099117/31791 | |
dc.description.abstract | Isoquinoline-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.extent | vii, 114 leaves, bound : 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.R4 | en_US |
dc.subject.lcsh | Isoquinoline | en_US |
dc.title | A new approach to the synthesis of substituted isoquinolines | 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 .R4 (Regular Loan) | |
dc.identifier.callnumber | Special Collections: AS38 .R4 (Non-Circulating) | |
etd.degree.name | Doctor of Philosophy | |
etd.degree.grantor | Texas Christian University | |