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Synthesis 2001(6): 0811-0827
DOI: 10.1055/s-2001-13398
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Pyrrolidinetrione Derivatives: Synthesis And Applications in Heterocyclic Chemistry

Barbara Zaleska*, Sławomir Lis
Department of Organic Chemistry, Jagiellonian University Kraków, ul. Ingardena 3, 30-060 Kraków, Poland
Fax: +48(1)26340515; e-Mail: zaleska@chemia.uj.edu.pl;
Further Information

Publication History

Received 7 February 2001
Publication Date:
15 October 2004 (online)

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Abstract

This review article, covering the literature from 1891 to 1999, deals with the methods of preparation of pyrrolidinetrione derivatives, emphasis being placed on methods of reasonable efficiency. A general applicability of these compounds as versatile building blocks in synthesis of fused heterocyclic systems is in focus.

  • 1 Introduction

  • 2 Synthesis of Pyrrolidinetrione Derivatives

  • 2.1 Pyrrolidine-2,3,5-trione Derivatives A, Substituted at C-4

  • 2.2 Pyrrolidine-2,3,5-trione Derivatives B with Exocyclic C = C at Position C-4

  • 2.3 Pyrrolidine-2-thioxo-4,5-dione Derivatives C

  • 2.4 Synthesis of Schiff Bases at C-6 of Pyrrolidine-2,3,5-trione Derivatives B and C

  • 2.5 Preparation of Pyrrolidine-2,3,4-trione Derivatives D

  • 3 Reactivity of Pyrrolidine-2,3,5-trione Derivatives

  • 3.1 Reactions of Pyrrolidine-2,3,5-triones with Monoamines

  • 3.2. Synthesis of Fused Heterocyclic Systems

  • 3.2.1 Reactions at C-3 and C-6 of Pyrrolidinetriones C

  • 3.2.2 Pyrrolo[3,4-c]pyrazole, pyrrolo[3,4-c]1,4-diazepine and Pyrrolo[3,4-f]1,5-diazocine

  • 3.3 Rearrangements and Ring Expansion of Pyrrolidinetrione Derivatives

  • 3.3.1 Furan-2,3-dione Derivatives

  • 3.3.2 Furo[3,4-c]pyridine Derivatives

  • 3.3.3 Pyrrolo[3,4-c]pyridine Derivatives

  • 3.3.4 Pyrroline-2,3-dione Derivatives

  • 3.3.5 Ring Expansion of Pyrrolidine-2,3,5-trione Derivatives to Quinoline Derivatives

  • 3.4 Pyrrolidine-2,3,5-triones in the Synthesis of Quinoxaline, Benzoxazine, Cyclopentanone and 1,2,4-Triazine Derivatives by Cyclocondensation at C-2 and C-3

  • 3.5 Heterocyclisation of Pyrrolidine-2,3,5-triones with Bifunctional Nucleophiles in Addition/Cyclization

  • 3.5.1 Synthesis of 1,3-Thiazine, Pyrimidine by Addition Reaction

  • 3.5.2 Reaction of Pyrrolidine-2,3,5-triones with Methylene-Active Compounds

  • 3.5.3 Reaction of Pyrrolidine-2,3,5-triones with Enaminocarbonyl Compounds

  • 3.5.4 Synthesis of 1,5-Benzodiazepine and 1,5-Benzothiazepine Derivatives

  • 3.5.5 4-Diazopyrrolidine-2,3,5-triones in the Synthesis of Pyrrolo[3.4-c]pyridazines

  • 3.6 Pyrrolidine-2,3,4-trione Derivatives in the Synthesis of Anellated Nitrogen-Containing 5,5-Ring Systems

  • 4 Hydrogenation of Pyrrolidine-2,3,5-triones

  • 5 Summary

Key words

pyrrolidinetrione - rearrangement - fused heterocyclic systems - hydrogenation - Schiff bases

    References

  • 1 Wislicenus W. Sattler W. Chem. Ber.  1891,  24:  1245 
    Google Scholar
  • 2 Howard EGJr. inventors; US  2,786,060. 
  • 3 Howard EGJr. inventors; US  2,832,790. 
  • 4 Schilling B, and Reutter A. inventors; DE  3305580 (Cl. C07D207/44). 
  • 5 Salmon-Legagner F. Oliver Y. Bobin C. Compt. Rend.  1964,  258 (26):  6456 
    Google Scholar
  • 6 Gerzon K. inventors; US  3.285-933. 
  • 8 Deubel HM, Walkenstein DG, von Dobeneck HH, Crosby J, and Milner JA. inventors; Brit. UK  2017690 (Cl. C07D413/02). 
  • 9 Figee T. Recl. Trav. Chim. Pays-Bas  1915,  34:  289 
    Google Scholar
  • 10 Stolle R. Luther M. Chem. Ber.  1920,  53:  314 
    Google Scholar
  • 11 Skinner GS. Perkins JFJr. J. Am. Chem. Soc.  1950,  72:  5569 
    CrossrefGoogle Scholar
  • 12 Sheehan JC. Corey J. J. Am. Chem. Soc.  1952,  74:  360 
    CrossrefGoogle Scholar
  • 13 Skinner GS. Wright EJ. J. Am. Chem. Soc.  1957,  79:  6204 
    CrossrefGoogle Scholar
  • 14 Howard EG. Kotch A. Lindsey RVJr. Putnam RE. J. Am. Chem. Soc.  1958,  80:  3924 
    CrossrefGoogle Scholar
  • 15a Merchant JR. Hakim MA. Pillay KS. J. Indian Chem. Soc.  1972,  49:  403 
    Google Scholar
  • 15b Merchant JR. Hakim MA. Pillay KS. J. Indian Chem. Soc.  1963,  40:  353 
    Google Scholar
  • 16 Skinner GS. Wright EJ. J. Am. Chem. Soc.  1957,  79:  6204 
    CrossrefGoogle Scholar
  • 17 Skinner GS. Miller CBJr. J. Am. Chem. Soc.  1953,  75:  977 
    CrossrefGoogle Scholar
  • 18 Harlay V. J. Pharm. Chim.  1936,  24:  537 
    Google Scholar
  • 19 Corey EJ. Schmidt G. Tetrahedron Lett.  1979,  5:  399 
    Google Scholar
  • 20 Capuano L. Bettinger A. Engel M. Pfordt M. Huch V. Liebigs Ann. Chem.  1988,  913 
    Google Scholar
  • 21 von Dobeneck H. Weil E. Bruner E. Liebigs Ann. Chem.  1978,  1424 
    Google Scholar
  • 22 Capuano L. Hell W. Wamprecht C. Liebigs Ann. Chem.  1986,  131 
    Google Scholar
  • 23 Karten MJ. Shapiro SL. Isaacs ES. Freeman L. J. Org. Chem.  1965,  60:  2657 
    Google Scholar
  • 24 Ř ankowska-JasiŇ ska W. Eilmes J. Rocz. Chem.  1973,  47:  2235 
    Google Scholar
  • 25 Řankowska-Jasi Ňska W. Zaleska B. Walocha K. Zesz. Nauk., Uniw. Jagiellon., Pr. Chem.  1973,  18:  137 
    Google Scholar
  • 26 Ř ankowska-JasiŇ ska W. Eilmes J. Rocz. Chem.  1976,  50:  1059 
    Google Scholar
  • 27 Řankowska-Jasi Ňska W. Zaleska B. Walocha K. Zesz. Nauk., Uniw. Jagiellon., Pr. Chem.  1976,  21:  135 
    Google Scholar
  • 28 Řankowska-Jasi Ňska W. Zaleska B. Walocha K. Rocz. Chem.  1977,  51:  915 
    Google Scholar
  • 29 Řankowska-Jasi Ňska W. Eilmes J. Zaleska B. Rocz. Chem.  1977,  51:  1617 
    Google Scholar
  • 30 Rosett T. Sankhala RS. Stickings CE. Taylor EU. Thomas R. Biochem. J.  1957,  67:  390 
    Google Scholar
  • 31 Jones RCF. Bhalay G. Carter PA. Duller KAM. Dunn SH. J. Chem. Soc., Perkin Trans. 1  1999,  7:  765 
    Google Scholar
  • 32 van der Baan JL. Barnick JWFK. Bickelhaupt H. Tetrahedron  1972,  34:  223 
    Google Scholar
  • 33 Holzapfel CW. Tetrahedron  1968,  24:  2101 
    CrossrefGoogle Scholar
  • 34 Reinhart KL. Beck JR. Borders DB. Kinstle T. Krauss D. J. Am. Chem. Soc.  1963,  85:  4038 
    CrossrefGoogle Scholar
  • 35 Yuki H. Kaizu Y. Yashida S. Takiura K. Chem. Pharm. Bull.  1971,  19:  1664 
    Google Scholar
  • 36 Yuki H. Kariya H. Hashimoto Y. Chem. Pharm. Bull.  1967,  15:  727 
    Google Scholar
  • 37 Harris SA. Fisher LV. Falkers K. J. Med. Chem.  1963,  8:  478 
    Google Scholar
  • 38 Jones RC. Sumura S. Tetrahedron Lett.  1978,  3173 
    CrossrefGoogle Scholar
  • 39 Yamaguchi T. Saito T. Yuki H. J. Heterocycl. Chem.  1976,  13:  533 
    CrossrefGoogle Scholar
  • 40 Saalfrank RW. Hörner B. Reck S. Nachtral J. Peters EM. Peters K. von Schnerung HG. Z. Naturforsch., B: Chem. Sci.  1996,  51:  1084 
    Google Scholar
  • 41 Sakamoto Y. Kurihara T. Yakugaku Zasshi  1979,  99:  818 
    Google Scholar
  • 42 Augustin M. Jeschke P. J. Prakt. Chem.  1987,  329:  649 
    Google Scholar
  • 43 Zaleska B. Walocha K. Rocz. Chem.  1976,  50:  251 
    Google Scholar
  • 44 Katritzky AR. Li QL. Fan WQ. J. Heterocycl. Chem.  1988,  25:  1287 
    Google Scholar
  • 45 Hebenbrock KF. Liebigs Ann. Chem.  1978,  320 
    Google Scholar
  • 46 Kirino Y. Southwick PL. Schuler RH. J. Am. Chem. Soc.  1974,  673 
    CrossrefGoogle Scholar
  • 47 Kimitoshi S. Tatsuaki Y. J. Chem. Soc., Perkin Trans. 2  1979,  1605 
    CrossrefGoogle Scholar
  • 48 Zaleska B. J. Pract. Chem.  1988,  330:  440 
    Google Scholar
  • 49 Ostrowska K. Ciechanowicz-Rutkowska M. Pilati T. Řuchowski G. Monatsh. Chem.  1999,  130:  555 
    CrossrefGoogle Scholar
  • 50 Zaleska B. Olech A. Řyczkowska T. Pol. J. Chem.  1982,  56:  1483 
    Google Scholar
  • 51 Řankowska-Jasi Ňska W. Ostrowska K. Pol. J. Chem.  1994,  68:  2627 
    Google Scholar
  • 52 Řankowska-Jasi Ňska W. Ostrowska K. J. Prakt. Chem.  1991,  333:  619 
    Google Scholar
  • 53 Řankowska-Jasi Ňska W. WodzieŇ M. Zesz. Nauk., Uniw. Jagiellon., Pr. Chem.  1989,  32:  75 
    Google Scholar
  • 54 Řankowska-Jasi Ňska W. WodzieŇ M. Wajda MP.   , 
  • 55 Řankowska-Jasi Ňska W. Borowiec H. Kolasa A. Zaleska B. Pol. J. Chem.  1985,  59:  169 
    Google Scholar
  • 56 Řankowska-Jasi Ňska W. Ostrowska K. J. Prakt. Chem.  1989,  331:  700 
    Google Scholar
  • 57 Řankowska-Jasi Ňska W. Borowiec H. BurgieŠ M. Góralik W. Walocha K. Zaleska B. Chojnacka-Wójcik E. Wiczyska B. Pol. J. Pharmacol. Pharm.  1986,  30:  309 
    Google Scholar
  • 59 Řankowska-Jasi Ňska W. Borowiec H. BurgieŠ M. Golus J. Góralik W. Kolasa A. Pol. J. Chem.  1985,  59:  159 
    Google Scholar
  • 60a Ostrowska K. Řankowska-JasiŇ ska W. Ciechanowicz-Rutkowska M. Pilati T. J. Chem. Res., Synop.  1996,  236 
    Google Scholar
  • 60b Ostrowska K. Řankowska-JasiŇska W. Ciechanowicz-Rutkowska M. Pilati T. J. Chem. Res., Miniprint  1996,  1352 
    Google Scholar
  • 61 Wahren M. Z. Chem.  1969,  9:  241 
    Google Scholar
  • 62 Zaleska B. J. Prakt. Chem.  1988,  330:  841 
    Google Scholar
  • 63 Zaleska B. Monatsh. Chem.  1986,  117:  671 
    CrossrefGoogle Scholar
  • 64 Zaleska B. J. Prakt. Chem.  1987,  329:  787 
    Google Scholar
  • 65 Andrejczikov JS. Chim. Get. Sed.  1975,  11:  1468 
    Google Scholar
  • 66 Murai S. Hasegawa K. Sonoda N. Angew. Chem.  1975,  87:  668 
    Google Scholar
  • 67 Ziegler E. Eder M. Belegratis C. Prewedourakis E. Monatsh. Chem.  1967,  98:  2249 
    Google Scholar
  • 68 Fatiadi JA. Synthesis  1978,  165 
    Article in Thieme ConnectGoogle Scholar
  • 69 Bogdanowicz-Szwed K. Monatsh. Chem.  1982,  113:  583 
    Google Scholar
  • 70 Zaleska B. Pol. J. Chem.  1984,  58:  469 
    Google Scholar
  • 71a Sano T. Toda J. Tsudo Y. Chem. Pharm. Bull.  1983,  31:  356 
    Google Scholar
  • 71b Sano T. Toda J. Tsudo Y. Chem. Pharm. Bull.  1984,  32:  497 
    Google Scholar
  • 71c Sano T. Toda J. Tsudo Y. Chem. Pharm. Bull.  1987,  35:  23 
    Google Scholar
  • 71d Sano T. Toda J. Tsudo Y. Chem. Pharm. Bull.  1987,  35:  479 
    Google Scholar
  • 72 Zaleska B. Kurdziel M. Synth. Comm.  1988,  18:  1863 
    Google Scholar
  • 73 Metwally MA. Sofan MA. Z. Naturforsch., B: Chem. Sci.  1990,  45:  382 
    Google Scholar
  • 74 Safan MA. Pharmazie  1997,  52:  276 
    Google Scholar
  • 75 Augustin M. Fischer G. Schneider B. Köhler M. J. Prakt. Chem.  1979,  321:  787 
    Google Scholar
  • 76 Augustin M. Jeschke P. J. Prakt. Chem.  1987,  329:  637 
    Google Scholar
  • 77 Augustin M. Jeschke P. J. Prakt. Chem.  1987,  329:  985 
    Google Scholar
  • 78 Augustin M. Jeschke P. J. Prakt. Chem.  1987,  329:  607 
    Google Scholar
  • 79 Augustin M. Jeschke P. Synthesis  1987,  10:  937 
    Article in Thieme ConnectGoogle Scholar
  • 80 Poschenrieder H. Stachel HD. J. Heterocycl. Chem.  1995,  32:  1457 
    CrossrefGoogle Scholar
  • 81 Szabo A. Künzle N. Mallat T. Baiker A. Tetrahedron: Asymmetry  1999,  10:  61 
    CrossrefGoogle Scholar
  • 82 Künzle N. Szabo A. Schürch M. Wang G. Mallat T. Baiker A. Chem. Commun.  1998,  1377 
    CrossrefGoogle Scholar
  • 83 Poll T. Abdel-Hady AF. Karge R. Linz G. Weetman J. Helmchen G. Tetrahedron Lett.  1989,  30:  5595 
    CrossrefGoogle Scholar
7

Deutsche Gold und Silver Scheidanstalt, Neth. Appl. 298,715, 1965; Ger. Appl., 1962.

58

Zaleska, B.; Lech, J.; in press.