Date of Award

Spring 1982

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Roy L. Williams

Committee Member

Frank E. Scully, Jr.

Committee Member

Billy T. Upchurch

Committee Member

Patricia A. Pleban

Call Number for Print

Special Collections LD4331.C45 H94

Abstract

A study was undertaken to examine the potential for ortho cyclization associated with the synthesis of 1,2,3,4,-tetrahydroisoquinolines using the Pictet-Spengler reaction. Specif1cally, the condensation of the biogenic amines, dopamine, norepinephrine and epinephrine were carefully examined in light of current literature and the facility and extent of ortho cyclization in each case. The para isomers of these three biogenic amine condensation products were isolated and characterized, while only the ortho isomer derived from dopamine was found stable and could be isolated, and structurally identified. These studies demonstrate that a second cyclization product does, in fact, form in each instance and that these products are less polar but much more unstable than the para isomer.

These "ortho" products were also shown to be fanned under physiological conditions in vitro and thus the possible involvement of such structures in certain disease states such as alcoholism now needs to be considered.

The formation of ortho cyclized tetrahydroisoquinolines was also extended to include an example in which 1-substituted tetrahydroisoquinolines were derived from the condensation of 6-hydroxydopamine with various carbonyl compounds.

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DOI

10.25777/xwdr-8k25

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