Synthesis and transformations of sulfides in the thiophene series 35. Synthesis of certain polyfunctional and condensed compounds derived from substituted acetals in the thiophene series
Metallation of diacetals of 5-substituted-2-alkylthio-3-thiophenecarboxaldehydes with butyllithium in ether proceeds at the freeβ-position of the thiophene ring, so that different polyfunctional derivatives of thiophene can be synthesized.
By the action of sodium in liquid ammonia on 5-methoxy-2-methylthio-3-thiophenecarboxaldehyde diethylacetal, and subsequent treatment with water, 5-methylthieno [3,2-d]isothiazole is formed.
Certain intracoordination compounds of Co(II), Ni(II), and Zn were obtained which include the thiophene ring substituted in the α-position with a methoxy group.
KeywordsSodium Acetal Ether Ammonia Sulfide
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- 1.Ya. L. Gol'dfarb and M. A. Kalik, Zh. Org. Khim.,14, 2603 (1978).Google Scholar
- 2.Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Zh. Obshch. Khim.,29, 3631 (1959).Google Scholar
- 3.A. W. Gschwend and H. R. Rodrigues, Organic Reactions, Vol. 26, Wiley, New York-London-Sydney-Toronto (1979), p. 43.Google Scholar
- 4.Ya. L. Gol'dfarb, M. A. Kalik, and V. K. Zav'yakova, Zh. Org. Khim.,15, 1540 (1979).Google Scholar
- 5.A. M. Fedorova, in: V. M. Rodionov, Selected Works [in Russian], Izd. Akad. Nauk SSSR, Moscow (1958), p. 123.Google Scholar
- 6.N. Meyer and D. Seebach, Chem. Ber.,113, 1304 (1980).Google Scholar
- 7.D. W. Slocum and C. A. Jennings, J. Org. Chem.,41, 3653 (1976).Google Scholar
- 8.Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Izv. Akad. Nauk SSSR, Ser. Khim., 701 (1962).Google Scholar
- 9.Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Khim. Geterotsikl. Soedin., 220 (1965).Google Scholar
- 10.L. V. Alam and I. Ya. Kvitko, Khim. Geterotsikl. Soedin., 561 (1978).Google Scholar
- 11.Ya. L. Gol'dfarb, M. A. Kalik, and V. K. Zav'yalova, Khim. Geterotsikl. Soedin., 182 (1981).Google Scholar
- 12.Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Izv. Akad. Nauk SSSR., Ser. Khim., 1769 (1969).Google Scholar