Introduction of substituents in the pyridine proton of 7-azaindoline
- 26 Downloads
Electropilic substitution (nitration, bromination, and chlorination) of 4-methyl-6-chloro-7-azaindoline (and its N-acetyl derivative) takes place in the 5 position. 4-Methyl-5-amino-7-azaindoline, 4-methyl-5-nitro-7-azaindoline, and 1-acetyl-4-methyl-5-amino-6-chloro-7-azaindoline were obtained by reduction of 1-acetyl-4-methyl-5-nitro-6-chloro-7-azaindoline under various conditions. A method was developed for the preparation of a new three-ring system — 1,2,3-oxadiazolo[5,4-b]-pyrrolo[2,3-e]pyridine.
KeywordsOrganic Chemistry Pyridine Nitration Pyridine Proton
Unable to display preview. Download preview PDF.
- 1.I. N. Palant, D. M. Krasnokut-skaya, K. F. Turchin, S. S. Anisimova, and Yu. I. Vainshtein, Khim. Geterotsikl. Soedin., No. 9, 1277 (1975).Google Scholar
- 2.M. M. Robison and B. L. Robison, J. Am. Chem. Soc. 78, 1247 (1956).Google Scholar
- 3.L. N. Yakhontov, V. A. Azimov, and E. I. Lapan, Tetrahedron Lett., 1909 (1969).Google Scholar
- 4.M. M. Robison, B. L. Robison, and F. P. Butler, J. Am. Chem. Soc., 81, 743 (1959).Google Scholar
- 5.L. N. Yakhontov, M. Ya. Uritskaya, and M. V. Rubtsov, Zh. Obshch. Khim., 34, 1449 (1964).Google Scholar
- 6.L. N. Yakhontov, Usp. Khim., 37, 1258 (1968).Google Scholar
- 7.D. M. Krasnokut-skaya and L. N. Yakhontov, Inventors' Certificate No. 453403 (1973); Byul. Izobr., No. 46, 55 (1974).Google Scholar