Synthesis and reactions in the 1,2,3,4-tetrahydroisoquinoline series.

  • Clive Robert Spray

Student thesis: Doctoral ThesisPhD


The work described in this thesis is divided into three chapters. Each chapter is preceded by an introduction which outlines the field of research described in the chapter and the reasons for pursuing the rationale for the research. Chapter I describes the synthesis of a series of 3,4,11,11a- tetrahydrobenzo [b] quinolizin-2 (6H)-ones (I) and their reactions, specifically with phenyl magnesium bromide. Further reactions of the carbonyl function are also discussed. Chapter II contains an investigation into the synthesis of suitable 2,3-disubstituted-l,2,3,4-tetrahydroisoquinolines on which to perform intramolecular Diels-Alder reactions. The successful intramolecular Diels-Alder reaction of two substrates is described and the stereochemistry of the products has been investigated. Chapter III is divided into two short sections, each preceded by an introduction. The first section describes a series of 1,3-dipolar cycloaddition reactions, utilizing 1,2,3,4-tetrahydroiso- quinoline-1- and -3-carboxylic acids as substrates. The second section involves the investigation of a series of 2,3-sigmatropic rearrangements of 2-substituted-l,2,3,4-tetrahydroisoquinoline-3-esters.
Date of Award1981
Original languageEnglish
Awarding Institution
  • University of Bath

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