Abstract
2,3-Dihydroperimidines are dehydrogenated smoothly by sodium pyrosulfite in refluxing aqueous alcohol, as a result of which the corresponding perimidines are formed in high yields. The reaction of 1,8-naphthalenediamine with the aldehydic forms of sugars gives 2-polyhydroxyalkyl-2,3-dihydroperimidines, which are also aromatized by sodium pyrosulfite to give the corresponding 2-polyhydroxyalkyl-perimidines in high yields.
Similar content being viewed by others
Literature cited
V. V. Kuz'menko, A. F. Pozharskii, and V. N. Komissarov, Khim. Geterotsikl. Soedin., No. 1, 93 (1980).
H. F. Ridley, R. G, W. Spickett, and G. M. Timmis, J. Heterocycl. Chem., 2, 453 (1965).
P. T. Tuason and S. L. Johnson, Biochemistry, 16, 1183 (1977).
H. W. Wood, Chem. Ind., 1119 (1955).
H. Remy, Treatise on Inorganic Chemistry [translated by J. S. Anderson], Vol. 1, Elsevier Publishing Co., New York (1956).
N. M. Starshikov, A. F. Pozharskii, and F. T. Pozharskii, Khim. Geterotsikl. Soedin., No. 7, 986 (1977).
V. Paragamian, M. B. Baker, B. M. Rima, and J. Reale, J. Heterocycl. Chem., 5, 591 (1968).
N. M. Starshikov and F. T. Pozharskii, Khim. Geterotsikl. Soedin., No. 7, 1001 (1973).
A. F. Pozharskii, L. P. Smirnova, B. A. Tertov, I. S. Kashparov, and V. I. Sokolov, Khim. Geterotsikl. Soedin., No. 12, 1682 (1975).
A. F. Pozharskii and I. S. Kashparov, Khim. Geterotsikl. Soedin., No. 1, 111 (1970).
J. S. Whitehurst, J. Chem. Soc., 226 (1951).
F. Sachs, Liebigs Ann., 365, 81 (1909).
N. P. Buu-Hoi, P. Jacquignon, and M. Marty, Bull. Soc. Chim. Fr., 461 (1960).
A. F. Pozharskii, N. M. Starshikov, F. T. Pozharskii, and Yu. I. Mandrykin, Khim. Geterotsikl. Soedin., No. 7, 980 (1977).
F. Sachs and M. Steiner, Ber., 42, 3764 (1909).
I. V. Komissarov, A. A. Konstantinchenko, A. F. Pozharskii, I. T. Filippov, and I. S. Kashparov, Khim.-Farm. Zh., No. 7, 28 (1976).
A. K. Sheinkman, A. F. Pozharskii, V. I. Sokolov, and T. V. Stupnikova, Dokl. Akad. Nauk SSSR, 226, 1094 (1976).
N. M. Starshikov and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 10, 1413 (1978).
A. V. Lizogub and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 1, 110 (1979).
H. Ohle, Ber., 67, 157 (1934).
A. F. Pozharskii and N. M. Starshikov, Khim. Geterotsikl. Soedin., No. 10, 1418 (1978).
V. I. Sokolov, A. F. Pozharskii, I. S. Kashparov, A. G. Ivanov, and B. I. Ardashev, Khim. Geterotsikl, Soedin., No. 4, 558 (1974).
G. F. Potemkin and Z. N. Nazarova, Methods for the Synthesis of Chemical Reagents and Preparations [in Russian], Vol. 22, Moscow (1970), p. 101.
A. V. Lizogub, A. F. Pozharskii, and V. I. Sokolov, Zh. Obshch. Khim., 46, 680 (1976).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 47.
Translated from Khimiya Geterotsikliches-kikh Soedinenii, No. 1, pp. 96–100, January, 1980.
Rights and permissions
About this article
Cite this article
Starshikov, N.M., Pozharskii, A.F. Heterocyclic analogs of pleiadiene. Chem Heterocycl Compd 16, 81–85 (1980). https://doi.org/10.1007/BF00475399
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00475399