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Alkylation of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones

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Abstract

Reaction of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with dimethyl sulfate and haloalkanes in DMF or DMSO in the presence of potassium hydroxide gives the 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones (N-substituted products) and 9,9a-dihydro-3H-imidazo[1,2-a]indoles (O-substituted products). The latter, on treatment with acids and bases, are converted into 1-alkoxycarbonylmethyl-2,3-dihydro-1H-indoles. 1-Ethoxycarbonyl-methyl-2,3-dihydro-1H-indoles on treatment with lithium aluminohydride undergoes cyclization to 2,3,9,9a-tetrahydrooxazolo[3,2-a]indole.

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Literature Cited

  1. A. A. Shachkus and Yu. A. Degutis, Khim. Geterotsikl. Soedin., No. 11, 1485 (1986).

    Google Scholar 

  2. A. Barton and U. D. Ollis (eds.), General Organic Chemistry [Russian translation], Khimiya, Moscow (1983), Vol. 4, p. 386.

    Google Scholar 

  3. K. Orito and T. Matsuzaki, Tetrahedron, 35, 1017 (1980).

    Google Scholar 

  4. G. G. Yakobson and N. E. Akhmetova, Synthesis., No. 3, 169 (1983).

    Google Scholar 

  5. J. Yamakawi, T. Ando, and T. Hanafusa, Chem. Lett., No. 8, 1143 (1981).

    Google Scholar 

  6. R. A. W. Johnstone and M. E. Rose, Tetrahedron, 35, 2169 (1979).

    Google Scholar 

  7. H. Itoh, T. Nakagawa, and A. Nitta, French Pat. App. 2 498 182; Chem. Abstr., 98, 71 505 (1983).

    Google Scholar 

  8. Yu. A. Degutis, A. A. Shachkus, and A. G. Urbonavichyus, Khim. Geterotsikl. Soedin., No. 7, 933 (1985).

    Google Scholar 

  9. M. A. Gal'bershtam, N. M. Przhiyalgoskaya, O. R. Khrolova, I. B. Lazarenko, G. K. Bobyleva, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 12, 1640 (1977).

    Google Scholar 

  10. Yu. A. Degutis and A. A. Shachkus, Khim. Geterotsikl. Soedin., No. 2, 227 (1987).

    Google Scholar 

  11. S. Carlsson and S.-O. Lawesson, Tetrahedron, 36, 3585 (1980.

    Google Scholar 

  12. S. Carlsson, A. A. El-Barbary, and S.-O. Lawesson, Bull. Soc. Chim. Belg., 89, 643 (1980).

    Google Scholar 

  13. E. Schmidt, West German Pat. No. 2 060 614; Ref. Zh. Khim., 2N231P (1981).

  14. M. Hayami and S. Torikoshi, US Pat. No. 4 314 058; Ref. Zh. Khim., 2N254P (1983).

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  1. Kaunas Snechkus Polytechnic Institute, 233006, Kaunas

    A. A. Shachkus & Yu. A. Degutis

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  1. A. A. Shachkus
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  2. Yu. A. Degutis
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 49–53, January, 1988.

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Shachkus, A.A., Degutis, Y.A. Alkylation of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones. Chem Heterocycl Compd 24, 41–44 (1988). https://doi.org/10.1007/BF00475563

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  • DOI: https://doi.org/10.1007/BF00475563

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