Abstract
We have synthesized 2-(p-methoxybenzylamino)-1-(p-R phenacyl)pyridinium bromides by alkylation of 2-R-(Pmethoxybenzylamino)pyridine with substituted phenacyl bromides. Using spectral methods we have shown that the title compounds exist in the form of 1, 2-diaryl-2-hydroxy-2, 3-dihydroimidazo[l, 2-alpyridinium salts. We have studied their properties and suggest an alternative synthesis route.
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References
A. E. Chichibabin, Zh. Russ. Fiz. Khim. Ob-va,58, 1159 (1926).
J. Allen and A. Tirot, J. Label. Compounds and Radiopharm.,23, 393 (1986).
P. J. Sanfilippo, M. Urbanski, and J. B. Press, J. Med. Chem.,31, 2221 (1988).
R. J. Sunberg, D. J. Dahlhausen, G. Manikumar, B. Mavunkel, A. Biswas, V. Srinivasan, F. King, Jr., and Ph. Waid, J. Heterocycl. Chem.,25, 129 (1988).
J. J. Kaminski, G. Puchalski, and D. M. Solomon, J. Med. Chem.,32, 1686 (1989).
Syntheses of Heterocyclic Compounds, No. VIII [in Russian], Izdat. Akad. Nauk Arm. SSR, Yerevan (1969), p. 49.
K. É. Valter, Ring-Chain Isomerism in Organic Chemistry [in Russian], Zinatne, Riga (1979).
A. J. Gordon and R. Ford, A Chemist's Companion [Russian translation], Mir, Moscow (1976), p. 541.
G. P. Claxton, J. M. Grisar, and N. L. Wiech, J. Med. Chem.,17, 364 (1974).
D. Garfinkel and F. T. Edsall, J. Am. Chem. Soc.,80, 3807 (1958).
T. F. Gallagher and J. L. Adams, Tetrahed. Lett.,30, 6599 (1989).
C. K. Bradsher, R. D. Brandan, and J. E. Boliek, J. Org. Chem.,34, 2129 (1969).
W. L. Mosby, Heterocyclic Systems With Bridgehead Nitrogen Atoms, Pt. 1, 747 (1961).
Additional information
T. G. Shevchenko Chernigov Pedagogical Institute, Chernigov 250038; Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 252660. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 644-649, May, 1995. Original article submitted December 27, 1994; revised, April 20, 1995.
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Demchenko, A.M., Chumakov, V.A., Nazarenko, K.G. et al. Synthesis, structure, and properties of 1-(p-R-phenacyl)-2-(p-methoxybenzylamino)pyridinium bromides. Chem Heterocycl Compd 31, 567–572 (1995). https://doi.org/10.1007/BF01166331
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DOI: https://doi.org/10.1007/BF01166331