Indole derivatives CXV. Synthesis and some transformations of 5-(3-indolyl)isoxazole-3-carboxylic acid
- 58 Downloads
5-(3-Indolyl)isoxazole-3-carboxylic acid and its amide and hydrazide were obtained from ethyl 5-(3-indolyl)isoxazole-3-carboxylate. When 5-(3-indolyl)isoxazole-3-carboxylate is heated, it undergoes decarboxylation with isomerization to 3-(ω-cyanoacetyl)indole; when it is heated in alcohol with hydrazine and phenylhydrazine in the presence of copper, it undergoes isomerization to 5-(3-indolyl)pyrazole-3-carboxylic and 1-phenyl-5-(3-indolyl)-pyrazole-3-carboxylic acids. 5-(3-Indolyl)pyrazole-3-carboxylic acid hydrazide is formed when a solution of ethyl 5-(3-indolyl)isoxazole-3-carboxylate is refluxed with hydrazine in 96% alcohol.
KeywordsCopper Alcohol Ethyl Organic Chemistry Amide
Unable to display preview. Download preview PDF.
- 1.B. Ya. Eryshev, T. D. Ershova, V. N. Buyanov, and N. N. Suvorov, Trudy MKhTI im. D. I. Mendeleeva, 94, 42 (1977).Google Scholar
- 2.G. I. Zhungietu and G. N. Dorofeenko, Usp. Khim., 41, 1627 (1972).Google Scholar
- 3.V. P. Gorbunova and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 11, 1519 (1973).Google Scholar
- 4.F. Millich and E. I. Becker, J. Org. Chem., 23, 1096 (1958).Google Scholar
- 5.S. R. Hiremath and R. S. Hosmane, Adv. Heterocycl. Chem., 15, 277 (1973).Google Scholar
- 6.S. D. Sokolov, I. M. Yudintsev, and P. V. Petrovskii, Zh. Org. Khim., 6, (1970).Google Scholar
- 7.L. Claisen, Ber., 36, 3671 (1903).Google Scholar
- 8.N. K. Kochetkov and S. D. Sokolov, Adv. Heterocycl. Chem., 2, 365 (1963).Google Scholar
- 9.S. Cusmano, Gazz. Chim. Ital., 70, 227 (1940).Google Scholar