Abstract
Imidazo[1,2-a]pyridines were obtained by direct reaction of acetophenone, propiophenone, and their furan analogs and ring-substituted derivatives with an equimolar amount of iodine and and excess 2-aminopyridine or its substituted derivatives. The effect of substituents in the ketones and 2-aminopyridine, the reagent molar ratios, the character of the solvents, and replacement of iodine by other halogenating agents on the course of the reaction and the yields of products was studied. The formation of 3-iodo- and 6-iodoimidazopyridines as side products was noted in the case of ketones that do not have electron-acceptor substituents in the ring. These and other iodo-substituted imidazopyridines were synthesized for chromatographic comparison.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. E. Chichibabin (Tschitschibabin), Ber.,58, 704 (1925).
A. E. Chichibabin, Zh. Russk. Khim. Obshchestva,57, 421 (1926).
L. C. King, J. Am. Chem. Soc.,66, 894 (1944).
L. C. King, J. Am. Chem. Soc..67, 2089 (1945).
L. C. King and M. Whirter, J. Am. Chem. Soc.,68, 717 (1946).
O. Magidson and G. Menschikoff, Ber.,58, 113 (1925).
A. S. Tomcufcik and L. N. Starker, in: Pyridine and Its Derivatives, Vol. 3 (ed. by Klingsberg), Interscience Publ. (1962), p. 36.
N. O. Saldabol, L. L. Zeligman, and S. A. Giller, Khim. Geterotsikl. Soedin., No. 6, 860 (1971).
N. O. Saldabol, L. L. Zeligman, and S. A. Giller, Khim. Geterotsikl. Soedin., No. 1, 37 (1973).
N. O. Saldabol, Khim. Geterotsikl. Soedin., No. 11, 1534 (1975).
R. A. Zingaro and W. E. Tolberg, J. Am. Chem. Soc.,81, 1353 (1959).
I. Haque and J. L. Wood, Spectrochim. Acta, A,23, 959, 2523 (1967).
N. O. Saldabol, L. L. Zeligman and S. A. Giller, Inventor's Certificate No. 407897 (1973); Byul. Izobr., No. 47, 82 (1973).
M. Portelli and G. Bartolini, Ann. Chim. (Rome),53, 1180 (1963).
Norwich Pharm. Co., US Patent No. 3105834 (1963); Chem. Abstr.,59, 8761 (1963).
E. Corey and J. P. Schaefer, J. Am. Chem. Soc.,82, 918 (1960).
J. Toullec and J. E. Dubois, Tetrahedron,29, 2851 (1973).
L. M. Litvinenko and L. A. Perel'man, Reakts. Sposobn. Org. Soedin.,8, 331 (1971).
L. M. Litvinenko, A. F. Popov, Zh. P. Gel'bina, and E. V. Kirillov, Reakts. Sposobn Org. Soedin.,10, 175 (1973).
N. O. Saldabol, S. A. Giller, L. N. Alekseeva, and B. A. Brizga, Khim.-Farmats. Zh., No. 2, 27 (1967).
N. O. Saldabol, S. A. Giller, L. N. Alekseeva, and I. V. Dipan, Khim.-Farmats. Zh., No. 6, 16 (1972).
N. O. Saldabol and Yu. Yu. Popelis, Khim. Geterotsikl. Soedin., No. 5, 691 (1972).
N. O. Saldabol, L. N. Alekseeva, B. A. Brizga, L. V. Kruzmetra, and S. A. Giller, Khim.-Farmats. Zh., No. 7, 19 (1970).
K. S. Dhaka, V. K. Chadra, and H. K. Pujari, Austral. J. Chem.,26, 436 (1973).
N. O. Saldabol and S. A. Giller, Izv. Akad. Nauk LatvSSR, No. 11, 91 (1958).
N. O. Saldabol, L. L. Zeligman, and L. A. Ritevskaya, Khim. Geterotsikl. Soedin., No. 9, 1208 (1975).
Author information
Authors and Affiliations
Additional information
Deceased.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1396–1405, October, 1976.
Rights and permissions
About this article
Cite this article
Saldabol, N.O., Giller, S.A. Synthesis of imidazo[1,2- a] pyridines directly from methyl or methylene ketones. iodination of imidazo[1,2-a] pyridines. Chem Heterocycl Compd 12, 1155–1162 (1976). https://doi.org/10.1007/BF00945605
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00945605