Synthesis of N-aryl-5-alkylidene-2,5-dihydropyrrol-2-ones by "cyclization/Dimroth rearrangement" reactions of 1,3-dicarbonyl dianions with diimidoyl dichlorides of oxalic acid

European Journal of Organic Chemistry

Volumn , Issue 9, 2004, Pages 1897-1910

  Anders, Joachim T ^a   Görls, Helmar ^b   Langer, Peter ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Cyclization; Dianions; Heterocycles; Oxalic acid derivatives; Regioselectivity

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CARBONYL DERIVATIVE; CHLORIDE; OXALIC ACID; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIMROTH REARRANGEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; LITHIATION; STEREOCHEMISTRY;

EID: 4544350050     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300727     Document Type: Article

References (69)

1. [1a] M. F. Grundon, Nat. Prod. Rep. 1987, 4, 89.
2. [1b] J. R. Lewis, Nat. Prod. Rep. 1993, 10, 291.
3. [1c] J. R. Lewis, Nat. Prod. Rep. 1994, 11, 329.
4. [1d] J. H. Rigby, R. C. Hughes, M. J. Heeg, J. Am. Chem. Soc. 1995, 117, 7834.
5. [2a] J. H. Rigby, Tetrahedron 1996, 52, 10569 and literature cited therein.
6. [2b] C. J. Simmons, F.-J. Marner, J. H. Cardellina, R. E. Moore, K. Seff, Tetrahedron Lett. 1979, 2003.
7. [2c] J. H. Cardellina, R. E. Moore, Tetrahedron Lett. 1979, 2007.
8. G. D. James, S. D. Mills, G. Pattenden, J. Chem. Soc., Perkin Trans. 1 1993, 2581.
9. [4a] W. D. Celmer, J. A. Salomons, J. Am. Chem. Soc. 1955, 77, 2861.
10. [4b] I. Dell, C. R. A. Godfrey, D. J. Wadsworth, in Synthesis and Chemistry of Agrochemicals III, ACS Symposium Series, 1992, 504, 384.
11. N. D. Abdullaev, K. Samikov, T. P. Antsupova, M. R. Yagudaev, S. Y. Yunusov, Chem. Nat. Compd. (Engl. Transl.) 1987, 23, 576.
12. Tetramic acid natural products: B. J. L. Royles, Chem. Rev. 1995, 95, 1981.
13. S. Hashiguchi, H. Natsugari, M. Ochiai, J. Chem. Soc., Perkin Trans. 1 1988, 2345.
14. Mitomycins: [8a] J. R. Luly, H. Rapoport, J. Am. Chem. Soc. 1983, 105, 2859.
15. [8b] J. Rebek Jr., S. H. Shaber, Y.-K. Shue, J.-C. Gehret, S. Zimmerman, J. Org. Chem. 1984, 49, 5164.
16. [9a] A. D. Abell, J. M. Taylor, J. Org. Chem. 1993, 58, 14 and references cited therein.
17. [9b] A. D. Abell, M. D. Oldham, J. M. Taylor, J. Org. Chem. 1995, 60, 1214.
18. W. V. Murray, P. Lalan, A. Gill, M. F. Addo, J. M. Lewis, D. K. H. Lee, M. P. Wachter, R. Rampulla, D. C. Underwood, Bioorg. Med. Chem. Lett. 1993, 369.
19. A. Barco, S. Benetti, G. P. Pollini, J. Org. Chem. 1979, 44, 1734.
20. W. Shen, C. A. Coburn, W. G. Bornmann, S. J. Danishefsky, J. Org. Chem. 1993, 58, 611.
21. P. Langer, I. Freifeld, Chem. Commun. 2002, 2668.
22. [14a] H. Falk, The Chemistry of Linear Oligopyrroles and Bile Pigments, Springer-Verlag, Wien 1989, p. 355.
23. [14b] C. J. Dutton, C. J. R. Fookes, A. R. Battersby, J. Chem. Soc., Chem. Commun. 1983, 1237.
24. [14c] F.-P. Montforts, U. M. Schwartz, Angew. Chem. 1985, 97, 767; Angew. Chem. Int. Ed. Engl. 1985, 24, 775.
25. [14c] F.-P. Montforts, U. M. Schwartz, Angew. Chem. 1985, 97, 767; Angew. Chem. Int. Ed. Engl. 1985, 24, 775.
26. [15a] O. W. Woltersdorf, S. J. de Solms, E. H. Schultz, E. J. Cragoe, J. Med. Chem. 1977, 20, 1400.
27. [15b] R. V. Stevens, L. E. DuPree Jr., W. L. Edmonson, L. L. Magid, M. P. Wentland, J. Am. Chem. Soc. 1971, 93, 663.
28. [15c] D. M. Arnott, A. R. Battersby, P. J. Harrison, G. B. Henderson, Z. C. Sheng, J. Chem. Soc., Chem. Commun. 1984, 525.
29. [16a] G. Stork, Y. Nakahara, Y. Nakahara, W. J. Greenlee, J. Am. Chem. Soc. 1978, 100, 7775.
30. [16b] G. Stork, E. Nakamura, J. Am. Chem. Soc. 1983, 105, 5510.
31. [17a] W. Flitsch, H. Peters, Chem. Ber. 1970, 103, 805.
32. [17b] W. Flitsch, S. R. Schindler, Synthesis 1975, 685.
33. [17c] P. J. Murphy, J. Brennan, Chem. Soc. Rev. 1988, 17, 1.
34. [17d] W. Flitsch, H. Peters, Chem. Ber. 1970, 103, 805.
35. J. D. White, R. A. Badger, H. S. Kezar III, A. J. Pallenberg, G. A. Schiehser, Tetrahedron 1989, 45, 6631, and references cited therein.
36. H.-D. Stachel, M. Schorp, L. Maier, K. Dandl, Liebigs Ann. Chem. 1994, 1121.
37. J. P. Celerier, E. Marx, G. Lhommet, J. Heterocycl. Chem. 1988, 25, 1275.
38. [21a] A. Müller, A. Maier, R. Neumann, G. Maas, Eur. J. Org. Chem. 1998, 1177.
39. [21b] V. Virmani, M. B. Nigam, P. C. Jaim, N. Anand, Indian J. Chem., Sect. B 1979, 17, 472.
40. [21c] N. Anand, J. Singh, Tetrahedron 1988, 44, 5975.
41. For reviews of work from our laboratory, see: [22a] P. Langer, M. Döring, Eur. J. Org. Chem. 2002, 221.
42. [22b] P. Langer, Chem. Eur. J. 2001, 7, 3858.
43. [22c] P. Langer, Synthesis 2002, 441.
44. [23a] P. Langer, M. Stoll, Angew. Chem. 1999, 111, 1919; Angew. Chem. Int. Ed. 1999, 38, 1803.
45. [23a] P. Langer, M. Stoll, Angew. Chem. 1999, 111, 1919; Angew. Chem. Int. Ed. 1999, 38, 1803.
46. [23b] P. Langer, T. Schneider, M. Stoll, Chem. Eur. J. 2000, 6, 3204.
47. [23c] P. Langer, T. Eckardt, T. Schneider, C. Göbel, R. Herbst-Irmer, J. Org. Chem. 2001, 66, 2222.
48. P. Langer, M. Döring, Synlett 2001, 1437.
49. For a review of sequential reactions, see: [25a] L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131.
50. For a review of sequential reactions, see: [25a] L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131.
51. For domino reactions, see: [25b] L. F. Tietze, Chem. Rev. 1996, 96, 115.
52. L. Weiler, J. Am. Chem. Soc. 1970, 92, 6702.
53. D. Lindauer, R. Beckert, M. Döring, P. Fehling, H. Görls, J. Prakt. Chem. 1995, 337, 143.
54. M. Basato, B. Corain, A. C. Veronese, F. D'Angeli, G. Valle, G. Zanotti, J. Org. Chem. 1984, 49, 4696.
55. [29a] J. Fetter, L. T. Giang, T. Czuppon, K. Lempert, M. Kajtar-Peredy, G. Czira, Tetrahedron 1994, 50, 4185.
56. [29b] M. S. Manhas, M. Ghosh, A. K. Bose, J. Org. Chem. 1990, 55, 575.
57. K. Siegel, R. Brückner, Chem. Eur. J. 1998, 4, 1116.
58. F. J. Vinick, Y. Pan, H. W. Gschwend, Tetrahedron Lett. 1978, 44, 4221.
59. P. Langer, I. Freifeld, Chem. Eur. J. 2001, 7, 565, and references cited therein.
60. T. H. Al-Tel, M. Meisenbach, W. Voelter, Liebigs Ann. 1995, 689.
61. S. Boatman, C. R. Hauser, J. Org. Chem. 1966, 31, 1785.
62. [35a] O. Dimroth, Justus Liebigs Ann. Chem. 1909, 364, 183.
63. [35b] R. N. Lacey, J. Chem. Soc. 1954, 845.
64. [35c] R. N. Warrener, E. N. Cain, Tetrahedron Lett. 1966, 3231.
65. [35d] M. Waren, Z. Chem. 1969, 241.
66. MOLEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, The Netherlands, 1990.
67. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467.
68. G. M. Sheldrick, SHELXL-97, University of Göttingen, Germany, 1997.
69. CCDC-198694 (for 3c) and -198695 (for 10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: + 44-1223-336-033; or deposit@ccdc.cam.ac.uk].