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Indoledione-indole rearrangement (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The indoledione-indole rearrangement, which occurs during the basic condensation ofortho-aminophenylcarbonyl compounds (ortho-aminophenylglyoxylic acid,ortho-aminoketones) with halomethylketones, is reviewed.

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References

  1. Russ. Pat. 696,016; M. A. Rekhter, V. I. Gorgos, L. M. Zorin, and G. I. Zhungietu,Byull. Izobret. No. 41 (1979).

  2. Russ. Pat. 702,010; M. A. Rekhter, V. I. Gorgos, and G. I. Zhungietu,Byull. Izobret., No. 45 (1979).

  3. Russ. Pat. 642, 306; M. A. Rekhter, L. M. Zorin, and G. I. Zhungietu,Byull. Izobret., No. 2 (1979).

  4. Belg. Pat. 637, 355;Chem. Abs.,62, 7731 (1965).

  5. G. I. Zhungietu and M. A. Rekhter,Isatins and Their Derivatives [in Russian] Ptiintsa, Kishinev (1977), p. 5.

    Google Scholar 

  6. D. St. C. Black and C. H. Wong,J. Chem. Soc. Chem. Commun., No. 4, 200 (1980).

    Article  Google Scholar 

  7. M. A. Rekhter, F. Z. Makaev, F. V. Babilev, G. N. Grushetskaya, and S. V. Rubakov,Khim. Geterotsikl. Soedin., No. 4, 483 (1966).

    Google Scholar 

  8. M. A. Yurovskaya, V. V. Druzhinina, and Yu. G. Bundel,Khim. Geterotsikl. Soedin., No. 8, 1130 (1982).

    Google Scholar 

  9. W. Anthony,J. Org. Chem.,31, 77 (1966).

    Google Scholar 

  10. M. A. Rekhter,Khim. Geterotsikl. Soedin., No. 5, 642 (1993).

    Google Scholar 

  11. V. I. Gorgos, L. M. Zorin, G. I. Zhungietu, and M. A. Rekhter,Izv. Akad. Nauk Moldav. SSR, Ser. Khim. I Biol. Nauk, No. 2, 61 (1981).

    Google Scholar 

  12. M. A. Rekhter,Khim. Geterotsikl. Soedin., No. 5, 642 (1993).

    Google Scholar 

  13. V. I. Gorgos, L. M. Zorin, G. I. Zhungietu, and M. A. Rekhter,Khim. Geterotsikl. Soedin., No. 11, 1490 (1983).

    Google Scholar 

  14. M. A. Rekhter, B. A. Rekhter, I. G. Yazlovetskii, and A. A. Panasenko,Khim. Geterotsikl. Soedin., No. 2, 276 (1998).

    Google Scholar 

  15. Russ. Pat. 2, 947, 603; M. A. Rekhter,Byull. Izobret. No. 31 (1995).

  16. G. I. Zhungietu, V. I. Gorgos, M. A. Rekhter, and A. I. Korpan',Izv. Akad. Nauk Moldav. SSR, Ser. Khim. I Biol. Nauk, No. 3, 57 (1980).

    Google Scholar 

  17. A. A. Panasenko, A. F. Kaprosh, O. M. Radul, and M. A. Rekhter,Izv. Akad. Nauk, Ser. Khim., No. 1, 66 (1994).

    Google Scholar 

  18. G. Tacconi, P. P. Righetti, and G. Desimoni,J. Prakt. Chem.,315, 339 (1973).

    Article  Google Scholar 

  19. D. White,Synth. Commun.,7, 559 (1977).

    Google Scholar 

  20. O. M. Radul, G. I. Zhungietu, M. A. Rekhter, and S. M. Bukhanyuk,Khim. Geterotsikl. Soedin., No. 11, 1562 (1980).

    Google Scholar 

  21. O. M. Radul, G. I. Zhungietu, M. A. Rekhter, and S. M. Bukhanyuk,Khim. Geterotsikl. Soedin., No. 3, 353 (1983).

    Google Scholar 

  22. A. D. Ainlly and R. Robinson,J. Chem. Soc., 1508 (1934). O. M. Radul, S. M. Bukhanyuk, M. A. Rekhter, and G. I. Zhungietu,Abs. 1st All-Union Conf. “Khimiya, biokhimiya i farmakologiya proizbodnykh indola” [Chemistry, biochemistry and pharmacology of indole derivatives], Tbilisi (1986), p. 38.

  23. O. M. Radul, S. M. Bukhanyuk, and M. A. Rekhter,Khim. Geterotsikl. Soedin., No. 8, 1131 (1985).

    Google Scholar 

  24. Russ. Pat. 825, 521; M. A. Rekhter, V. I. Gorgos, and G. I. Zhungietu,Byull. Izobret., No. 16 (1981).

  25. Russ. Pat. 810, 686; L. M. Zorin, G. I. Zhungietu, and M. A. Rekhter,Byull. Izobret., No. 9 (1981).

  26. A. N. Kost, S. M. Korbunova, A. P. Blasova, V. N. Kiselev, and V. I. Gorbunova,Khim.-Farm. Zh., No. 2, 8 (1974).

    Google Scholar 

  27. L. M. Zorin, M. A. Rekhter, and G. I. Zhungietu,Syntheses of Heterocyclic Compounds [in Russian], Pt. 15, 56 (1985).

    Google Scholar 

  28. O. M. Radul, S. M. Bukhanyuk, M. A. Rekhter, and G. I. Zhungietu,Syntheses of Heterocyclic Compounds [in Russian], Pt. 14, 39 (1984).

    Google Scholar 

  29. A. I. Potopal'skii, L. V. Lozyuk, A. N. Mirolyubova, and B. F. Bessarabov,Antiviral, Anticancer and Antileucosis Preparations of Isatizone [in Russian], Naukova Dumka, Kiev (1991).

    Google Scholar 

  30. G. I. Zhungietu, L. M. Zorin, V. I. Gorgos, and M. A. Rekhter,Khim. Geterotsikl. Soedin., No. 8, 1064 (1982).

    Google Scholar 

  31. Kh. Sh. Khariton, G. I. Zhungietu, M. A. Rekhter, B. T. Oloi, and N. I. Chmiykhova,Khim. Geterotsikl. Soedin., No. 7, 957 (1975).

    Google Scholar 

  32. G. I. Zhungietu, N. I. Chmykhova, M. A. Rekhter, and Kh. Sh. Khariton,Khim. Geterotsikl. Soedin., No. 5, 639 (1977).

    Google Scholar 

  33. G. I. Zhungietu N. I. Chmykhova, M. A. Rekhter, and Kh. Sh. Khariton,Khim. Geterotsikl. Soedin., No. 5, 642 (1977).

    Google Scholar 

  34. Kh. Sh. Khariton, M. A. Rekhter, G. I. Zhungietu, N. I. Chmykhova and E. T. Oloi,Khim. Geterotsikl. Soedin., No. 1, 77 (1979).

    Google Scholar 

  35. N. P. Dormydontova, G. I. Zhungietu, and M. A. Rekhter,Abs. 1 st All-Union Conf. “Khimiya, biokhimiya i farmakologiya proizbodnykh indola” [Chemistry, biochemistry and pharmacology of indole derivatives], Tbilisi (1986), p. 62.

  36. O. M. Radul, S. M. Bukhanyuk, and M. A. Rekhter,Izv. Akad. Nauk Respub. Moldova. Biol. Khim. Nauki, No. 1, 47 (1992).

    Google Scholar 

  37. V. I. Votyakov, M. N. Shashikhina, S. V. Zhavrid, G. I. Zhungietu, M. A. Rekhter, G. E. Muntyan, L. M. Zorin, O. M. Radul, A. N. Kraskovskii, A. B. Roman, G. S. Gritsenko, N. L. Gril', A. E. Lipkin, V. M. Plakunov, R. S. Belen'kaya, T. I. Zileeva, and Yu. D. Churkin,Khim.-Farm. Zh., No. 11 30 (1978).

    Google Scholar 

  38. S. V. Zhavrid, M. N. Shashikhina, N. V. Gribkova, N. F. Kazak, A. I. Mikhaleva, B. A. Trofimov, A. N. Vasil'ev, G. I. Zhungietu, M. A. Rekhter, O. M. Radul, L. A. Vlad, S. M. Bukhanyuk, and L. M. Zorin,Khim.-Farm. Zh., No. 2, 25 (1983).

    Google Scholar 

  39. V. D. Mikazhan, M. L. Érenshtein, V. A. Grinberg, M. A. Rekhter, and G. I. Zhungietu,Abs. 1 st All-Union Conf. “Khimiya, biokhimiya i farmakologiya proizbodnykh indola” [Chemistry, biochemistry and pharmacology of indole derivatives], Tbilisi (1986), p. 100.

  40. S. V. Zhavrid, M. N. Shashikhina, N. V. Gribkova, N. F. Kazak, A. I. Mikhaleva, B. A. Trofimov, G. I. Zhungietu, M. A. Rekhter, S. M. Bukhanyuk, L. M. Zorin, and V. I. Shvedov,Abs. 5 th All-Union Coll. “Khimiya, biokhimiya i farmakologiya proizbodnykh indola” [Chemistry, biochemistry and pharmacology of indole derivatives], Tbilisi (1981), p. 165.

  41. N. P. Dormidontova, R. N. Vaskan, G. I. Zhungietu, M. A. Rekhter, B. P. Sukhanyuk, V. I. Votyakov, M. N. Shashikhina, S. V. Zhavrid, S. V. Khlyustov, and E. I. Boreko,Izv. Akad. Nauk Moldav. SSR, Ser. Biol. i Khim. Nauk, No. 4, 59 (1990).

    Google Scholar 

  42. M. A. Rekhter, B. A. Rekhter, I. G. Yazlovetskii, A. A. Panasenko, and F. Z. Makaev,Khim. Geterotsikl. Soedin., No. 3, 308 (1998).

    Google Scholar 

  43. C. D. Jones and T. Suarez,J. Org. Chem.,37, 3622 (1972).

    Article  Google Scholar 

  44. G. Kempter and E. Schiewald,J. Prakt. Chem.,28, 169 (1965).

    Article  Google Scholar 

  45. B. A. Rekhter and M. A. Rekhter,Khim. Geterotsikl. Soedin., No. 4, 561 (1998).

    Google Scholar 

  46. M. A. Rekhter, G. N. Grushetskaya, A. A. Panasenko, and M. Z. Krimer,Khim. Geterotsikl. Soedin., No. 2, 266 (1993).

    Google Scholar 

  47. M. A. Rekhter, G. N. Grushetskaya, A. A. Panasenko and M. Z. Krimer,Khim. Geterotsikl. Soedin., No. 7, 910 (1995).

    Google Scholar 

  48. M.-G. A. Shvekhgeiter,Khim. Geterotsikl. Soedin., No. 3, 291 (1996).

    Google Scholar 

  49. I. K. Moiseev, M. N. Zemtsova, and N. V. Makarova,Khim. Geterotsikl. Soedin., No. 7, 867 (1994).

    Google Scholar 

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Institute of Biological Plant Protection, Academy of Sciences of the Moldavian Republic, Kishinev 2058. Translated from Khimiya Geteorotsiklicheskikh Soedinenii, No. 9, pp. 1170–1180, September, 1998.

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Rekhter, M.A. Indoledione-indole rearrangement (review). Chem Heterocycl Compd 34, 1001–1010 (1998). https://doi.org/10.1007/BF02251543

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