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Aminolysis of sucrose. VIII. Formation mechanism of heterocyclic compounds

I. Ježo and I. Lužák

Slovak Academy of Sciences, Bratislava 9


Abstract: cf. CA 64, 8277c. The reaction of aq. sucrose solns. with NH3 in an autoclave at 140° and 220° was studied by paper chromatography. In addn. to the homologs of pyrazine and imidazole, 2-methyl-, 2,5-dimethyl-, and 2,6-dimethylpyrazine and 4(5)-methyl-, and 4(5)-hydroxymethylimidazole, the presence of 2-methyl-5-(D-arabino-tetrahydroxybutyl)pyrazine, m. 198-200° (abs. EtOH), [α]23D -60.8° (c 1, H2O), Rf 0.53; 2-methyl-6-(D-arabino-tetrahydroxybutyl)pyrazine, m. 169-70° (abs. EtOH), [α]23D -68° (c 1, H2O), Rf 0.55; 2-methyl-5-(D-arabino-tetrahydroxybutyl)-3-(D-erythro-trihydroxypropyl)pyrazine, m. 151-2° (abs. EtOH), [α]23D -100° (c 1, H2O), Rf 0.495; 4(5)-(D-arabino-tetrahydroxybutyl)imidazole, m. 162-3° (H2O), [α]23D -18.7° (c 1, H2O), Rf 01346; 2,5-bis(D-arabino-tetrahydroxybutyl)pyrazine, m. 234-5° (abs. EtOH), [α]23D -74.8° (c 1, H2O), Rf 0.243; 2-amino-2-deoxy-D-glucose, m. 129-32° (abs. EtOH), [α]23D 93° (c 1, CHCl3), Rf 0.153, and a compd. of the general compn. C12H23NO10(?), m. 85-7.5° (abs. MeOH), [α]23D 41.8° (c 1, CHCl3), Rf 0.114, were detd. It was detd. that by increasing temp. up to 220°, there is an increase in the pyrazine and imidazole fractions with a simultaneous decrease of the polyhydroxyalkyl derivs. of the heterocyclic compds. indicating a thermal cleavage of the side chains. Contrary to the reports in the literature, the formation of the imidazole derivs. is not dependent on the presence of the catalysts and CH2O (Parrod, CA 25, 3968) and on the presence of the fragmentation products of the sucrose (Windaus and Langenbeck, CA 17, 2884).

Full paper in Portable Document Format: 208a586.pdf (in Slovak)


Chemical Papers 20 (8) 586–594 (1966)

Monday, April 19, 2021

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