Synthesis of new pyrazole and isoxazole derivatives based on products of condensation of β-dicarbonyl compounds with 1,2,3-trihalopropanes
The reaction of 2-(2-halo-3-propenyl)-1,3-dicarbonyl compounds, which are formed in the alkylation of Β-dicarbonyl compounds with 1,2,3-trihalopropanes in the presence of potassium carbonate in DMSO, with hydrazine and hydroxylamine derivatives was studied. The synthesis of new pyrazole and isoxazole derivatives on the basis of this reaction is described. Some chemical transformations of the 1,2-azoles obtained were investigated.
KeywordsPotassium DMSO Organic Chemistry Hydrazine Alkylation
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- 1.A. N. Kost and I. I. Grandberg, Adv. Heterocycl. Chem., 6, 327 (1966).Google Scholar
- 2.N. K. Kochetkov and S. D. Sokolov, Adv. Heterocycl. Chem., 2, 365 (1963).Google Scholar
- 3.N. S. Zefirov, S. I. Kozhushkov, and T. S. Kuznetsova, Tetrahedron, 38, 1693 (1982).Google Scholar
- 4.A. P. Kozikowski and P. D. Stein, J. Am. Chem. Soc., 104, 4023 (1982).Google Scholar
- 5.J. G. Buchanan, A. Stobie, and R. H. Wightman, J. Chem. Soc., Chem. Commun., 916 (1980).Google Scholar
- 6.Sh. T. Akhmedov, N. S. Sadykhov, V. M. Ismailov, M. A. Akhundova, N. K. Sadovaya, F. N. Karimov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., No. 10, 1428 (1984).Google Scholar
- 7.M. R. Grimmet, in: General Organic Chemistry [in Russian], N. K. Kochetkov (ed.), Vol. 8 Khimiya, Moscow (1985), p. 442.Google Scholar
- 8.S. D. Sokolov, T. N. Egorova, and P. V. Petrovskii, Khim. Geterotsikl. Soedin., No. 5, 602 (1974).Google Scholar
- 9.Organicum [Russian translation], Vol. 1, Mir, Moscow (1979), p. 316.Google Scholar
- 10.N. S. Zefirov, S. I. Kozhushkov, and T. S. Kuznetsova, Khim. Geterotsikl. Soedin., No. 6, 807 (1983).Google Scholar
- 11.A. M. Berkengeim, The Chemistry and Technology of Synthetic Medicinals [in Russian], Joint Scientific and Technical Publishing House, Moscow (1935), p. 328.Google Scholar