Abstract
The reaction of dimedone with salicyl and 2-hydroxy-1-naphthoyl aldehydes gave derivatives of tetrahydroxanthene and tetrahydrobenzo[a]xanthene and not aldimedone as occurs in condensations with other aldehydes. Derivatives of decahydroacridine were obtained by reaction of the tetrahydroxanthene derivatives with methyl-and ethylamine. Tetrahydro- and octahydroxanthene derivatives were obtained from the reaction of acetylsalicylaldehyde with dimedone in acetic anhydride. The structures of the ketoenol forms of the products containing aβ-ketoenol unit were determined by1H and13C NMR spectroscopy, and the mechanism of their interconversion is discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. Fieser and M. Fieser, Reagents for Organic Synthesis [Russian translation], Vol, 1, Mir, Moscow (1974), p. 300.
D. Barton and V. D. Ollis (eds.), General Organic Chemistry [Russian translation], Vol. 2, Khimiya, Moscow (1982), p. 516.
A. N. Nesmeyanov and N. A. Nesmeyanov, Principles of Organic Chemistry [in Russian], Vol. 1, Khimiya, Moscow (1969), p. 557.
A. S. Roska, M. K. Klyavin'sh, and A. Kh. Zitsmanis, Izv. Akad. Nauk Latv. SSR. Ser. Khim., No. 1, 97 (1988).
R. Elderfield (ed.), Heterocyclic Compounds [Russian translation], Vol. 7, Mir, Moscow (1965), p. 57.
Y. Rachedi, M. Hamdi, and V. Speziale, Synth. Commun.,20, No. 18, 2827 (1990).
O. Ya. Neiland, Ya. P. Stradyn', É. A. Silinysh, D. R. Balode, S. P. Valtere, V. P. Kadysh, S. V. Kalnin', V. É. Kampar, I. B. Mazheika, and L. F. Taure, Structure and Tautomerism ofβ-Dicarbonyl Compounds [in Russian], Zinatne, Riga (1977), p. 84.
B. I. Ionin, B. A. Ershov, and A. I. Kol'tsov, NMR Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningrad (1983), p. 221.
I. G. Zilnietse and A. Kh. Zitsmanis, Izv. Akad. Nauk. Latv. SSR. Ser. Khim., No. 5, 616 (1984).
Ya. Ya. Ozols, A. N. Pyrko, B. A. Vigante, R. R. Dubure, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 5, 631 (1992).
Additional information
Institute of Bioorganic Chemistry, Belarus Academy of Science, Minsk, 220141. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 742–753, June, 1996. Original article submitted February 22, 1996.
Rights and permissions
About this article
Cite this article
Pyrko, A.N. Synthesis of tetra- and octahydroxanthene derivatives by the condensation of dimedone with aromatic aldehydes. Chem Heterocycl Compd 32, 635–645 (1996). https://doi.org/10.1007/BF01164861
Issue Date:
DOI: https://doi.org/10.1007/BF01164861