Abstract
The reaction of 2-aminomethylaniline with 1,3-dicarbonyl compounds gives a series of 1,2,3,4-tetrahydroquinazoline derivatives. A ring-chain tautomeric equilibrium of the type enamine-1,2,3,4-tetrahydroquinazoline is observed in solutions of these compounds and its position depends of the structure of the starting dicarbonyl component and the solvent polarity.
Similar content being viewed by others
REFERENCES
G. Kempter, H.-J. Ziegner, G. Moser, and W. Natho, Wiss. Z. Pädagog. Hochsch. Karl Liebknecht, Potsdam, 21, 5 (1977).
J. J. van den Eynde, J. Godin, A. Mayence, A. Maquestiau, and E. Anders, Synthesis, 9, 867 (1993).
J. Lessel, Arch. Pharm. (Weinheim), 327, 329 (1994).
L. Lazar and F. Fülöp, Eur. J. Org. Chem., 3025 (2003).
J. Sinkkonen, K. N. Zelenin, A. A. Potapov, I. V. Lagoda, V. V. Alekseyev, and K. Pihlaja, Tetrahedron, 59, 1939 (2003).
K. N. Zelenin, A. A. Potapov, I. V. Lagoda, V. V. Alekseyev, Ya. Sinkkonen, and K. Pihlaja, Khim. Geterotsikl. Soedin., 1305 (2002).
S. I. Yakimovich and K. N. Zelenin, Zh. Obshch. Khim., 65, 705 (1995).
S. I. Yakimovich and I. V. Zerova, Enamines in Organic Synthesis, Sverdlovsk, (1989), p. 90.
Ya. F. Freimanis, The Chemistry of Enamino Ketones, Enamino Imines, and Enamino Thiones, Zinatne, Riga, (1974), 274 p.
S. I. Yakimovich, V. N. Nikolaev, and N. V. Koshmina, Zh. Org. Khim., 18, 1173 (1982).
S. I. Yakimovich, I. V. Zerova, and K. N. Zelenin, Ross. Khim. Zh., 43, 115 (1999).
Rights and permissions
About this article
Cite this article
Zelenin, K.N., Potapov, A.A., Alekseyev, V.V. et al. Ring-Chain Tautomerism of 1,2,3,4-Tetrahydroquinazolines. The Products of Reaction of 1,3-Dicarbonyl Compounds with 2-Aminomethylaniline. Chemistry of Heterocyclic Compounds 40, 903–910 (2004). https://doi.org/10.1023/B:COHC.0000044573.19543.09
Issue Date:
DOI: https://doi.org/10.1023/B:COHC.0000044573.19543.09