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Synthesis of 1,3-thiazoline derivatives from β-dicarbonyl compounds and phenacyl thiocyanate

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Russian Chemical Bulletin Aims and scope

Abstract

Acetylacetone and ethyl acetoacetate undergo addition at the C≡N bond of phenacyl thiocyanate in the presence of Ni(acac)2 to give the respective keteneN, S-acetals, which undergo smooth cyclization to afford 2-methylene-4-phenyl-1, 3-thiazoline derivatives when refluxed in THF.

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References

  1. V. A. Dorokhov, M. F. Gordeev, E. M. Shashkova, A. V. Komkov, and V. S. Bogdanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2600 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 2274 (Engl. Transl.)].

  2. M. F. Gordeev, A. V. Komkov, and V. A. Dorokhov,Khim. Geterotsikl. Soedin., 1990, 1286 [Chem. Heterocycl. Comp. USSR, 1990 (Engl. Transl.)].

  3. V. A. Dorokhov, M. F. Gordeev, A. V. Komkov, and V. S. Bogdanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2593 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 2267 (Engl. Transl.)].

  4. Z. K. Dem'yanets,Ph. D. Chem. Thes., Inst, of Organ. Chem., USSR Acad. Sci., Moscow, 1991 (in Russian).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    V. A. Dorokhov, M. F. Gordeev, E. M. Shashkova & V. S. Bogdanov

Authors
  1. V. A. Dorokhov
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  2. M. F. Gordeev
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  3. E. M. Shashkova
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  4. V. S. Bogdanov
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1938–1940, November, 1993

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Dorokhov, V.A., Gordeev, M.F., Shashkova, E.M. et al. Synthesis of 1,3-thiazoline derivatives from β-dicarbonyl compounds and phenacyl thiocyanate. Russ Chem Bull 42, 1854–1856 (1993). https://doi.org/10.1007/BF00699002

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  • DOI: https://doi.org/10.1007/BF00699002

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