Formation and characterization of a multicomponent equilibrium system derived from cis- and trans-1-aminomethylcyclohexane-1,2-diol

Hetenyi, A [Hetényi, Anasztázia (NMR spektroszkópi...), szerző] Gyógyszerkémiai Intézet (SZTE / GYTK); Szakonyi, Z [Szakonyi, Zsolt (szerves- és gyógy...), szerző] Gyógyszerkémiai Intézet (SZTE / GYTK); Klika, K D; Pihlaja, K; Fulop, F [Fülöp, Ferenc (Kémia), szerző] Gyógyszerkémiai Intézet (SZTE / GYTK)

Angol nyelvű Tudományos Szakcikk (Folyóiratcikk)
Megjelent: JOURNAL OF ORGANIC CHEMISTRY 0022-3263 1520-6904 68 (6) pp. 2175-2182 2003
  • SJR Scopus - Organic Chemistry: D1
    Both cis and trans isomers of amino diols 3-6 were prepared stereoselectively. In the reactions between 3-6 and phenyl isothiocyanate, the ring closure proceeded regioselectively and resulted only in spiro derivatives of 2-phenyliminooxazolidines 9, 10, 13, and 14. The reaction of cis- (or trans-)1-aminomethylcyclohexane-1,2-diol 4 (or 6) with 1 equiv of an aromatic aldehyde 15a-g in EtOH at room temperature resulted in a complex, multicomponent equilibrium mixture of 16a-g and 18a-g (or 17a-g and 19a-g), in each case consisting of a five-component, ring-chain tautomeric system 16A-E (or 17A-E), involving the Schiff base, two epimeric spirooxazolidines, two epimeric condensed 1,3-oxazines, and some of the four tricyclic compounds 18A-D (or 19A-D). The five-component, ring-chain equilibria were found to be adequately described by the Hammett-Brown linear free energy equation.
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    2020-08-13 04:41