Abstract
The methylene group of 5-methyl-4-ethyl-2-propanonyl-thiazol (II) reacts with different aldehydes yielding theKnoevenagel-condensation products (1–14). The reactions ofII with amines or ammonia gives exclusively the enamines as demonstrated by the1H-NMR-spectrum (15–23). The reaction product fromII with ammonia (23) can be further transformed to the corresponding derivatives of urea (24–27) with isocyanates.II reacts with acylchlorides in pyridine to the 0-acylation compounds (28–32) and with isocyanates to the corresponding urethanes (38–40).
Similar content being viewed by others
Literatur
96. Mitt.:Asinger F.,Schmitz M. K., Monatsh. Chem., im Druck.
Asinger F., Schröder L., Hoffmann S., Ann. Chem.648, 83 (1961).
Kotschetkow N. K., [Nachr. Akad. Wiss. (UdSSR) Abt. chem. Wiss.]1953, 991; C. A.49, 2308 (1955).Nessmejanow A. N.,Kotschetkow N. K.,Rybinskaja M. J., [Nachr. Akad. Wiss. (UdSSR), Abt. chem. Wiss.]1954, 741; C.A.50, 5802 (1956).Nessmejanow A. N.,Kotschetkow N. K.,Rybinskaja M. J., [Nachr. Akad. Wiss. (UdSSR), Abt. chem. Wiss.]1950, 350; C.A.47, 3035 (1951).Nessmejanow A. N.,Kotschetkow N. K.,Dombrovskij Ja. V., [Nachr. Akad. Wiss. (UdSSR), Abt. chem. Wiss.]1955, 179; C.A.50, 1577/d (1956).
Asinger F., Thiel M., Angew. Chem.70, 667 (1958).Asinger F., Schäfer W., Herkelmann G., Ann. Chem.672, 179 (1964).
Asinger F., Thiel M., Pallas E., Ann. Chem.602, 37 (1957).Asinger F., Thiel M., Kaltwasser H., Ann. Chem.606, 67 (1957).Asinger F., Thiel M., Kalzendorf I., Ann. Chem.610, 25 (1957).
Organikum, 15. Aufl., S. 590. Berlin: VEB Deutscher Verlag der Wissenschaften. 1977.
Vgl. z. B.Bucherer H. T., Lieb V. A., J. prakt. Chem. [2]141, 5 (1934).
Asinger F., Thiel M., Esser G., Ann. Chem.610, 33 (1957).
Asinger F., Thiel M., Schröder L., Ann. Chem.610, 49 (1957).
Mowry D. T.,Ringwald E. L., Org. Synthesis27, 91. J. Amer. Chem. Soc.72, 2037 (1950).
Franke W., Kraft R., Angew. Chem.67, 395 (1955).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Asinger, F., Wadehn, J. & Giesbertz, K. Zur Kenntnis der Reaktionsfähigkeit des 5-Methyl-4-ethyl-2-propanonyl-thiazols. Monatsh Chem 113, 1311–1319 (1982). https://doi.org/10.1007/BF00808746
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00808746