Abstract
The chemical behavior of 9-R-sym-octahydroxanthene-1,8-diones and salts based on them in recyclization reactions under the influence of amines was studied. The effect of the basicity of the amines on the direction of recyclization was established. A method is proposed for the single-stage synthesis of sym-octahydroacridine-1.8-dione oximes based on 1,8-dioxo-sym-octahydroxanthenes. Conditions were worked out for the oxidation of sym-octahydroxanthene-1,8-diones and N-R-decahydroacridinediones to the corresponding salts.
Similar content being viewed by others
References
A. Ya. Strakov, E. Yu. Gudrinietse, and D. R. Zitsane, Khim. Geterotsikl. Soedin., 1011 (1974).
K. Nagarajan and S. J. Shenoy, Indian J. Chem., 31A, No. 2, 73 (1992).
H. H. Lehz and M. Mitrovic, US Patent 3414587; Chem. Abstr., 70, 57648 (1969).
W. Kirkor and S. Rychter, Soc. Scient. Lodz. Acta Chim., No. 11, 91 (1966).
H. Antaki, J. Chem. Soc., 4877 (1963).
H. Antaki, J. Chem. Soc., 2263 (1965).
M. Seth and A. P. Bhaduri, Indian J. Chem., 15B, No. 2, 196 (1977).
A. A. Bakibaev, Zh. Org. Khim., 27, 1519 (1991).
Yu. M. Shchekotikhin, Yu. A. Getmanenko, T. G. Nikolaeva, and A. P. Kriven’ko, Khim. Geterotsikl. Soedin., 1344 (2001).
M. V. Mel’nik, M. Yu. Kornilov, A. V. Turov, and B. M. Gutsulyak, Zh. Org. Khim., 18, 1460 (1982).
T. G. Nikolaeva, Yu. M. Shchekotikhin, A. S. Ponomarev, and A. P. Kriven’ko, Khim. Geterotsikl. Soedin., 475 (2000).
O. H. Mattson and G. Sundström, Acta Chem. Scand., 24, 2267 (1970).
I. O. Edafiogho, C. N. Hinko, N. Chang, J. A. Moore, D. Mulzac, J. M. Nicholson, and K. R. Scott, J. Med Chem., 32, 2798 (1992).
N. Srividya, P. Ramamurthy, P. Shanmugasundaram, and V. T. Ramakrishnan, J. Org. Chem., 61, 5083 (1996).
N. Martin, M. Quinteiro, C. Seoane, J. L. Soto, A. Mora, M. Suarez, E. Ochoa, A. Morales, and R. S. del Bosq, J. Heterocycl. Chem., 32, 235 (1994).
G. Ya. Vanag and E. I. Stankevich, Zh. Obshch. Khim., 30, 3287 (1960).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 32–38, January, 2006.
Rights and permissions
About this article
Cite this article
Shchekotikhin, Y.M., Nikolaeva, T.G. Transformations of sym-octahydroxanthene-1,8-diones and 1,8-dioxo-sym-octahydroxanthylium salts in recyclization under the influence of amines. Chem Heterocycl Compd 42, 28–33 (2006). https://doi.org/10.1007/s10593-006-0042-1
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0042-1