Abstract
Hydrolysis of the 4-alkyliminothiopyrano[2,3-b]pyridinedioles (5) and 4-alkylaminothiopyrano[2,3-b]pyridones (6) resp. with 10% NaOH gives 5,7-dihydroxy-2H-thiopyrano[2,3-b]pyridine-4(3H)-one (7).7 can be obtained in better yield by reaction of 4-dimethylamino-2(1H)-pyridinethione (8) with bistrichlorphenylethylamlonate (2). Aminolysis of7 affords the two isomeric products5 and6. On treatment with hydrazines,7 reacts only to 4-hydrazonoderivatives5. By heating in bromobenzene5d is cyclisized to 1H-5,1,2,6-thiatriaza-acenaphthylen-7-ol (11). On methylation with methyljodide5,6 and7 furnish the 7-methoxyproducts13,14 and12. By heating in 20% NaOH7 is transformed into the 2-thioxo-3-pyridylmethylketone16 A and its tautomer, 2-mercapto-3-pyridylmethylketone16 B. The structures of5,6 and7 are discussed.
Similar content being viewed by others
Literatur
Zigeuner G., Schweiger K., Habernig D., Monatsh. Chem.113, 573 (1982).
Schweiger K., Habernig D., Schramm H.-W., Zigeuner G., Monatsh. Chem.114, 79 (1983).
Zigeuner G., Schweiger K., Fuchsgruber A., Monatsh. Chem.112, 187 (1981).
Wahren M., Z. Chem.9, 241 (1969).
Schweiger K., Monatsh. Chem.113, 1283 (1982).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Zigeuner, G., Schweiger, K. & Schramm, HW. Chemie des 5,7-Dihydroxy-2H-thiopyrano[2,3-b]pyridin-4(3H)-ons. Monatsh Chem 114, 923–935 (1983). https://doi.org/10.1007/BF00799953
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00799953