Synthesis of methyl-substituted benzofuro-, benzothieno-, and benzoselenopheno[2,3-b]pyridines
- 33 Downloads
Three-ring systems with benzo[b]furan, benzo[b]selenophene, and benzo[b]thiophene rings condensed with the pyridine ring and with a methyl group in the α position of the pyridine ring were synthesized by the reaction of 2-chloro-3-nitro-6-methylpyridine with sodium phenoxide, sodium thiophenoxide, or sodium selenophenoxide, reduction of the resulting 2-phenoxy-, 2-phenylthio-, and 2-phenylseleno-3-nitro-6-methylpyridines with stannous chloride in concentrated hydrochloric acid, diazotization of the substituted 3-aminopyridines, and heating of the diazonium compounds in 25% sulfuric acid.
KeywordsSodium Methyl Pyridine Sulfuric Acid Hydrochloric Acid
Unable to display preview. Download preview PDF.
- 1.V. G. Zhiryakov and P. I. Abramenko, Khim. Geterotsikl. Soedin., 334 (1965).Google Scholar
- 2.N. K. Kochetkov, Dokl. Akad. Nauk SSSR, 84, 289 (1952).Google Scholar
- 3.E. D. Parker and W. Shive, J. Am. Chem. Soc., 69, 63 (1947).Google Scholar
- 4.H. E. Baumgarten, H. Chien-Fan Su, J. Am. Chem. Soc., 74, 3828 (1952).Google Scholar
- 5.H. Gilman, M. Weston, Van Ess, and D. M. Hayes, J. Am. Chem. Soc., 61, 643 (1939).Google Scholar