Process for the production of specific isomer mixtures from oxin

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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548407, 548409, 548410, 548411, 546 47, 546 48, 546 49, 546 50, C07D20954, C07D20996, C07D47100, C07D49100, C07D49800, C07D51300

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057236259

ABSTRACT:
To produce defined isomer mixtures of compounds with spirocyclic beta-aminocarboxyl and/or beta-aminocarbonyl systems the invention supposes that they be dissolved in solvents which have good dissolving power for these compounds, whose relative permittivity is sufficient to stabilize the amphoteric intermediates occuring in isomerization, which as proton donors constitute hydrogen bridges, whose basicity is less than that of the compounds for isomerization and whose boiling point is so high that an adequate reaction speed can be attained by raising temperature. Further, the invention proposes that the isomerization be prevented, influenced, or terminated by altering at least one of these factors and or by altering the temperature.

REFERENCES:
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Aust. J. Chem., No. 21, pp. 491-504, A.F. Beecham et al., "The Stereochemistry of Oxindole Alkaloids: Uncarines A, B (Formosanine), C (Pteropodine), D (Speciophylline), E (Isopteropodine), and F" (Austrialia 1968).
Phytochemistry, vol. 12, pp. 2795-2798, J. David Phillipson, Sarah R. Hemingway, "Oxindole Alkaloids From Uncaria macrophylla" (England 1973).
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