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Synthesis of Heterocyclic Compounds Containing Perfluoroalkyl Groups. Reactions of Perfluoro(2-methyl-2-pentene) and Perfluoro(5-aza-4-nonene) with N,S-Dinucleophiles

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Abstract

Perfluoro(2-methyl-2-pentene) and perfluoro(5-aza-4-nonene) react with 1,4,5,6-tetrahydropyrimi-dine-2-thiol, pyridine-2-thiol, and 1,2,4-triazole-3-thiol to afford fused heterocyclic systems, while their reactions with tetrahydrothiazole-2-thione and pyrimidine-2-thiol result in replacement of the fluorine atom at the double bond. Treatment of 3,3,3-trifluoro-1-pentafluoroethyl-2-trifluoromethyl-1-pentenyl isothiocyanate with ammonia gives N-(3,3,3-trifluoro-1-pentafluoroethyl-2-trifluoromethyl-1-propenyl)thiourea which undergoes ring closure to 4-tetrafluoroethylidene-5,5-bis(trifluoromethyl)-4,5-dihydrothiazol-2-amine. Possible cyclization paths and the effect of the 1,3(N,S)-dinucleophile nature on the direction of nucleophilic addition at the double bond are discussed.

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REFERENCES

  1. Furin, G.G., Ftorsoderzhashchie geterotsiklicheskie soedineniya (Fluorine-Containing Heterocyclic Compounds), Novosibirsk: Nauka, 2001, p. 304.

    Google Scholar 

  2. Lekarstvennye sredstva (Medicines), Mashkovskii, M.D., Ed., Khar’kov: Torsing, 1998, vol. 1, p. 59; vol. 2, p. 592.

    Google Scholar 

  3. Filler, R. and Kobayashi, Y., Biomedical Aspects of Fluorine Chemistry, Tokyo: Kodansha Elsevier Biomed., 1982, p. 237.

    Google Scholar 

  4. Burger, K., Wucherpfenning, U., and Bunner, E., Adv. Heterocycl. Chem., 1994, vol. 60, p. 1.

    CAS  Google Scholar 

  5. Furin, G.G. and Gatilov, Yu.V., Khim. Geterotsikl. Soedin., 1993, p. 253.

  6. Furin, G.G., Pressman, L.S., Rogoza, A.V., and Salmanov, I.A., Russ. J. Org. Chem., 1997, vol. 33, p. 720.

    CAS  Google Scholar 

  7. Chi, K.-W., Kim, H.-A., Lee, W., Park, T.-H., Lee, U., and Furin, G.G., Bull. Korean Chem. Soc., 2002, vol. 23, p. 1017.

    CAS  Google Scholar 

  8. Rogoza, A.V., Furin, G.G., Gatilov, Yu.V., and Bagryanskaya, I.Yu., Izv. Ross. Akad. Nauk, Ser. Khim., 2001, p. 1027.

  9. Furin, G.G., Bagryanskaya, I.Yu., and Gatilov, Yu.V., Izv. Ross. Akad. Nauk, Ser. Khim., 1997, p. 1300.

  10. Rogoza, A.V. and Furin, G.G., Russ. J. Gen. Chem., 1999, vol. 69, p. 1433.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    G. G. Furin

  2. Novosibirsk State University, ul. Pirogova 2, 630090, Novosibirsk, Russia

    E. L. Zhuzhgov

Authors
  1. G. G. Furin
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  2. E. L. Zhuzhgov
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 441–446.

Original Russian Text Copyright © 2005 by Furin, Zhuzhgov.

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Furin, G.G., Zhuzhgov, E.L. Synthesis of Heterocyclic Compounds Containing Perfluoroalkyl Groups. Reactions of Perfluoro(2-methyl-2-pentene) and Perfluoro(5-aza-4-nonene) with N,S-Dinucleophiles. Russ J Org Chem 41, 434–439 (2005). https://doi.org/10.1007/s11178-005-0183-1

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  • DOI: https://doi.org/10.1007/s11178-005-0183-1

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