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Russian Journal of Organic Chemistry

, Volume 53, Issue 5, pp 796–799 | Cite as

8-(furan-2-yl)-4,5-dihydroacenaphtho[5,4-d]thiazole. Synthesis and reactions of electrophilic substitution

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Abstract

Condensation of 1,2-dihydroacenaphthylen-5-amine with furoyl chloride in 2-propanol afforded N-(1,2-dihydroacenaphthylen-5-yl)furan-2-carboxamide, whose treatment with excess P2S5 in anhydrous toluene led to the formation of the corresponding thioamide, and the oxidation with potassium ferricyanide in alkaline medium by Jacobson procedure resulted in 8-(furan-2-yl)-4,5-dihydroacenaphtho[5,4-d]thiazole. The latter was brought into electrophilic substitution reactions: nitration, bromination, formylation, acylation. Depending on the reaction conditions either the furan ring or the acenaphthene fragment suffer the attack.

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References

  1. 1.
    Pozharskii, A.F., Soldatenkov, A.T., and Katritzky, A.R., Heterocycles in Life and Society, Chichester J. Wiley & Sons, 1997.Google Scholar
  2. 2.
    Maruyama, T., Kuroki, N., and Konishi, K., Kogyo Kagaku Zasshi, 1965, vol. 68, p. 2428.CrossRefGoogle Scholar
  3. 3.
    Illenzeer, E.V., Aleksandrov, A.A., and El’chaninov, M.M., Russ. J. Org. Chem., 2012, vol. 48, p. 968. doi 10.1134/S1070428012070135CrossRefGoogle Scholar
  4. 4.
    Jacobson, P., Ber., 1886, vol. 19, p. 1067, 1811. doi 10.1002/cber.18860190237CrossRefGoogle Scholar
  5. 5.
    El’chaninov, M.M., Doctoral (Chem.) Dissertation, Rostov-on-Don, 2006.Google Scholar
  6. 6.
    Achkasova, A.A. and El’chaninov, M.M., Chem. Heterocycl. Compd., 2006, vol. 42, p. 166. doi 10.1007/s10593-006-0065-7CrossRefGoogle Scholar

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© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  1. 1.Platov South-Russian State Polytechnic UniversityNovosibirskRussia

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