Browsing by Author "G. Hardy"

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    Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. 11.' Alcohols Derived from 6,14-endo-Etheno- and 6,14-endo-Ethanotetrahydrothebaine
    (2012-11-20) K. W. Bentley; G. Hardy; B. Meek
    A series of secondary and tertiary alcohols have been prepared by the reduction and reaction with Grignard reagents of the aldehyde I (R = H), the ketones I (R = Me, Et, n-Pr, and Ph), and their 6,14-ethano analogs. The stereospecificity of the reactions is explained. In this way analgesics of very high potency, up to 500 times that of morphine, have been obtained
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    Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. I. Ketones Derived from 6,14-endo-Ethenotetrahydrothebaine
    (2012-11-14) K. W. Bentley; G. Hardy
    Several ketones I1 derived from 6,14-endo-ethenotetrahydrothebaine have been prepared by the Diels- Alder addition of certain a,P-unsaturated ketones to thebaine, by the action of cadmium alkyls on the corresponding acid chloride I1 (R = Cl), and, in some cases, by the action of Grignard reagents on the corresponding ester I1 (R =OEt) which is the adduct of thebaine and ethyl acrylate. Both 7a and 70 forms of the ketone I1 (R = Me), the ester I1 (R = OEt), and the nitrile 111 have been isolated. Attempts to convert the 7a ketone TI (R = Me) into the 7/3 isomer have resulted only in the formation of a keto1 X (R = H). Many of the bases prepared in this work are potent analgesics. The reaction product obtained from thebaine methiodide and p-benzoquinone has been shown to be a charge-transfer complex and not a true Diels-Alder adduct