Abstract
A method for peri-annulation of the pyridine or pyran ring to acridine was developed and used to obtain 7H-pyrido-and 7H-pyrano[2,3,4-kl]acridin-2(3H)-ones. The peri-groups were formed by a reaction of 9-chloro-1-nitroacridine with a CH-acid (malononitrile, ethyl cyanoacetate, and ethyl malonate) followed by reduction of the nitro group, or by a reaction of 1-amino-10-methylacridone with PCl5 and then with a CH-acid. Replacement of the chlorine atom in 9-chloro-1-methoxyacridines by the residue of the CH-acid with subsequent heating in an acidic medium afforded 7H-pyrano[2,3,4-kl]acridin-2(3H)-ones, which belong to a novel heterocyclic system.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. V. Gorelik, S. P. Titova, and E. V. Gordievskaya, Izv. Akad. Nauk, Ser. Khim., 2006, 1433 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1487].
M. Alvarez, L. Feliu, W. Ajana, J. A. Joule, and J. L. Fernandez-Puentes, Eur. J. Org. Chem., 2000, 849.
M. V. Gorelik, S. P. Titova, and T. Kh. Gladysheva, Izv. Akad. Nauk, Ser. Khim., 1998, 1179 [Russ. Chem. Bull., 1998, 47, 1147 (Engl. Transl.)].
T. Ozturk and A. McKillop, Can. J. Chem., 2000, 78, 1158.
J. M. F. Gagan, in Acridines, Ed. R. M. Acheson, 2nd ed., Wiley, New York, 1973, 218.
A. T. Troshchenko, Zh. Obshch. Khim., 1958, 28, 2207 [J. Gen. Chem. USSR, 1958, 28 (Engl. Transl.)].
N. S. Drozdov and N. S. Lezneva, Zh. Obshch. Khim., 1935, 5, 690 [J. Gen. Chem. USSR, 1935, 5 (Engl. Transl.)].
M. V. Gorelik, Zh. Org. Khim., 1968, 4, 513 [J. Org. Chem. USSR, 1968, 4, 505 (Engl. Transl.)].
D. K. C. Hodgeman and R. H. Prager, Aust. J. Chem., 1972, 25, 191.
K. Lehmstedt and K. Schrader, Ber., 1937, 70, 838.
S. M. Sherlin, G. I. Braz, A. Ya. Yakubovich, E. I. Vorob’eva, and F. E. Rabinovich, Zh. Obshch. Khim., 1938, 8, 884 [J. Gen. Chem. USSR, 1938, 8 (Engl. Transl.)].
M. Jonescu and J. Mester, Rev. Roum. Chim., 1969, 14, 789; Chem. Abstr., 1970, 72, 21787.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1605–1610, September, 2006.
Rights and permissions
About this article
Cite this article
Gorelik, M.V., Titova, S.P. & Gordievskaya, E.V. Syntheses of 7H-pyrido-and 7H-pyrano[2,3,4-kl]acridin-2(3H)-ones from 9-chloroacridines. Russ Chem Bull 55, 1664–1669 (2006). https://doi.org/10.1007/s11172-006-0471-0
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0471-0