Thesis-1978-Powell.pdf (10.94 MB)
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Studies in isoquinoline chemistry relating to morphine analgesics

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thesis
posted on 16.08.2018, 14:11 by Michael J. Powell
Approaches to the synthesis of partially hydrogenated 8-ketoisoquinolines have been made via 5,6,7,8-tetrahydroisoquinoline and also via attempted Bischler–Napieralski cyclodehydration of a series of 3-oxygenated cyclohexenyl-phenylacetamide derivatives. This latter ring closure has been found not to take, place and the former route also did not prove satisfactory. The synthesis of ring-A bridged isoquinolines has been studied. Although thermal isomerisation of 2,5-dihydrophenylacetamides to give conjugated dienes followed by Diels–Alder reaction met with limited success, the Diels–Alder reaction of 1,2,3,4,7,8-hexahydro-6-methoxy-2-methylisoquinoline has been achieved with methyl vinyl ketone, phenyl vinyl ketone and 2-chloroacrylonitrile. The exo- and endo-cycloadducts have been separated by column- and thin-layer chromatography and their stereochemistry assigned on the basis of n.m.r. studies. [Continues.]

Funding

Science Research Council and Reckitt and Colman Ltd, Pharmaceutical Division (Hull) (CASE research studentship).

History

School

  • Science

Department

  • Chemistry

Publisher

© Michael Joseph Powell

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

1978

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

en

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