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Synthesis of 5,6-indolo-12-crown-4 ethers

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Abstract

o-Alkyl derivatives of N-acetylaminobenzo-12-crowns-4 4a—f were prepared by Pd—Cu-catalyzed alkynylation of 5"-N-acetylamino-4"-iodobenzo-12-crown-4 (2). Cyclization of compounds 4a—f afforded the corresponding substituted 5,6-indolo-12-crowns-4 5a—c.

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References

  1. C. J. Pedersen, J. Am. Chem. Soc., 1967, 89, 7017.

    Google Scholar 

  2. M. Hiraoka, Crown Compounds, Kodansha Ltd., Tokyo; Elsevier Scientific Publishing Company, Amsterdam-Oxford-New York, 1982.

    Google Scholar 

  3. J. S. Bradshaw and R. M. Izatt, Acc. Chem. Res., 1997, 30, 338.

    Google Scholar 

  4. J. E. Saxton, The Chemistry of Heterocyclic Compounds, Wiley, New York, 1983, 25, Part IV.

    Google Scholar 

  5. K. C. Joshi and P. Chand, Pharmazie, 1982, 37, 1.

    Google Scholar 

  6. S. I. Zhungiettu, Oksiindol i ego proizvodnye [Hydroxyindole and Its Derivatives], Ed. G. V. Lazur´evskii, Shtiintsa, Kishinev, 1973, 195 pp. (in Russian).

    Google Scholar 

  7. C. E. Castro, E. J. Gaughan, and D. S. Owsley, J. Org. Chem., 1966, 31, 4071.

    Google Scholar 

  8. C. F. Vasilevsky, T. V. Anisimova, and M. S. Shvartsberg, Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 688 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983, 32, 626 (Engl. Transl.)].

    Google Scholar 

  9. J. Fujiwara, Y. Fukutani, H. Sano, K. Maruoka, and H. Yamamoto, J. Am. Chem. Soc., 1983, 105, 7177.

    Google Scholar 

  10. J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzales, J. Org. Chem., 1996, 61, 5804.

    Google Scholar 

  11. E. C. Taylor, A. H. Katz, H. Salgado-Zamora, and A. McKillop, Tetrahedron Lett., 1985, 26, 5963.

    Google Scholar 

  12. A. Arcadi, S. Cacchi, and F. Marinelli, Tetrahedron Lett., 1989, 30, 2581.

    Google Scholar 

  13. D. Rudisill and J. K. Stille, J. Org. Chem., 1989, 54, 5856.

    Google Scholar 

  14. S. F. Vasilevsky and M. S. Shvartsberg, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 2089 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 1901 (Engl. Transl.)].

  15. E. M. Hyde, B. L. Shaw, and I. Shepherd, J. Chem. Soc., Dalton Trans., 1978, 1696.

  16. N. A. Bumagin, A. B. Ponomaryov, and I. P. Beletskaya, Synthesis, 1984, 728.

  17. W. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280.

    Google Scholar 

  18. K. Sonogashira, Y. Tohda, and N. A. Hagihara, Tetrahedron Lett., 1975, 50, 4467.

    Google Scholar 

  19. S. Horiie, Nippon Kagaku Zasshi, 1958, 79, 227.

    Google Scholar 

  20. J. Reisch, Chem. Ber., 1964, 97, 2717.

    Google Scholar 

  21. T. Sakamoto, Y. Kondo, and H. Yamanaka, Heterocycles, 1986, 24, 31.

    Google Scholar 

  22. E. V. Tretyakov, S. V. Klyatskaya, and S. F. Vasilevskii, Izv. Akad. Nauk, Ser. Khim., 2000, 1415 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1409].

    Google Scholar 

  23. M. S. Shvartsberg, A. A. Moroz, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1971, 1306 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971, 20, 1209 (Engl. Transl.)].

    Google Scholar 

  24. P. Fitton and E. A. Rick, J. Organomet. Chem., 1971, 28, 277.

    Google Scholar 

  25. A. T. Allen and C. D. Cook, Can. J. Chem., 1963, 1984.

  26. L. Brandsma, S. F. Vasilevsky, and H. D. Verkruijsse, Application of Transition Metal Catalysts in Organic Synthesis, Springer Verlag, Heidelberg-Berlin-New-York, 1998, 335 pp.

    Google Scholar 

  27. V. P. Gorodnyuk, R. Ya. Grigorash, G. N. Chuprin, and S. A. Kotlyar, Zh. Obshch. Khim., 1998, 68, 1051 [J. Gen. Chem. USSR, 1998, 68 (Engl. Transl.)].

    Google Scholar 

  28. A. J. Gordon and R. A. Ford, The Chemist´s Companion. The Handbook of Practical Data, Techniques and References, New York-London-Sydney-Toronto, 1972.

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Klyatskaya, S.V., Tretyakov, E.V. & Vasilevsky, S.F. Synthesis of 5,6-indolo-12-crown-4 ethers. Russian Chemical Bulletin 51, 135–138 (2002). https://doi.org/10.1023/A:1015078217485

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