Regioselective anionic [3+2] cyclizations of imidazole dinucleophiles with oxaldiimidoyl dichlorides - A combined experimental and theoretical study

European Journal of Organic Chemistry

Volumn , Issue 12, 2001, Pages 2245-2255

  Langer, Peter ^a   Wuckelt, Jörg ^b   Döring, Manfred ^b   Schreiner, Peter R ^a,c   Görls, Helmar ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^c UNIVERSITY OF GEORGIA   (United States)

Author keywords

Cyclizations; Nitrogen heterocycles; Regioselectivity; Semiempirical calculations

Indexed keywords

1H PYRROLO[1,2 A]BENZIMIDAZOLE DERIVATIVE; 2,3 DIHYDROTHIAZOLO[3,2 A]BENZIMIDAZOLE DERIVATIVE; 3H IMIDAZO[1,2 A]BENZIMIDAZOLE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; DIAZABICYCLO[2.2.1]HEPTANONE DERIVATIVE; IMIDAZOLE DERIVATIVE; OXALDIIMIDOYL DICHLORIDE DERIVATIVE; OXALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS; THEORETICAL STUDY;

EID: 0034968989     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200106)2001:12<2245::AID-EJOC2245>3.0.CO;2-C     Document Type: Article

References (69)

1. [1a] A. J. Charlson, J. S. Harrington, Carbohydr. Res. 1972, 43, 383.
2. [1b] H. G. Alpermann, Arzneim.-Forsch. 1966, 16, 1641.
3. [1c] R. Zhou, E. B. Skibo, J. Med. Chem. 1996, 39, 4321.
4. [2a] P. Beak, J. L. Miesel, J. Am. Chem. Soc. 1967, 84, 2375.
5. [2b] G. P. Claxton, J. M. Grisar, N. L. Wiech, J. Med. Chem. 1974, 17, 364.
6. [2c] J. H. M. Hill, T. R. Fogg, H. J. Guttmann, J. Org. Chem. 1975, 40, 2562.
7. [3a] M. D. Nair, R. Adams, J. Am. Chem. Soc. 1961, 83, 3518.
8. [3b] R. Huisgen, H. Rist, Justus Liebigs Ann. Chem. 1955, 594, 159.
9. For literature related to imidazoles and benzimidazoles, see: [4a] J. R. McClure, J. H. Custer, H. D. Schwarz, D. A. Lill, Synlett 2000, 710.
10. [4b] A. R. Katritzky, C. N. Fali, J. Li, J. Org. Chem. 1997, 62, 4148.
11. For the extrusion of CO in the reaction between glycols and oxalyl dichloride, see: T. Iida, T. Itaya, Tetrahedron 1993, 49, 10511.
12. For cyclization reactions of dianions, see, for example: [6a] K. G. Bilyard, P. J. Garratt, R. Hunter, E. Lete, J. Org. Chem. 1982, 47, 4731.
13. [6b] R. B. Bates, B. Gordon, T. K. Highsmith, J. J. White, J. Org. Chem. 1984, 49, 2981.
14. [6c] K. Tanaka, H. Horiuchi, H. Yoda, J. Org. Chem. 1989, 54, 63.
15. [6d] D. Seebach, M. Pohmakotr, Tetrahedron 1981, 37, 4047.
16. [6e] A. Maercker, A. Groos, Angew. Chem. 1996, 108, 216;
17. Angew. Chem. Int. Ed. Engl. 1996, 35, 210.
18. [6f] A. Maercker, M. Theis, Top. Curr. Chem. 1987, 138, 1.
19. [6g] J. Vollhardt, H.-J. Gais, L. Lukas, Angew. Chem. Int. Ed. Engl. 1985, 24, 608. By "dianions" we refer to systems bearing two delocalized negative charges, the generation of which involves at least one abstraction of a proton attached to a carbon atom.
20. For recent cyclization reactions between dianion equivalents and 1,2-dielectrophiles from our laboratory, see: [7a] P. Langer, E. Holtz, Angew. Chem. 2000, 112, 3208;
21. Angew. Chem. Int. Ed. 2000, 39, 3086.
22. [7b] P. Langer, T. Eckardt, Angew. Chem. 2000, 112, 4503;
23. Angew. Chem. Int. Ed. 2000, 39, 4343.
24. [7c] P. Langer, T. Krummel, Chem. Commun. 2000, 967.
25. [7d] P. Langer, I. Freifeld, E. Holtz, Synlett 2000, 501.
26. [7e] P. Langer, I. Freifeld, Chem. Eur. J. 2001, 7, 565.
27. [7f] P. Langer, T. Schneider, Synlett 2000, 497.
28. [7g] P. Langer, J. Wuckelt, M. Döring, J. Org. Chem. 2000, 65, 729.
29. [7h] P. Langer, J. Wuckelt, M. Döring, H. Görls, J. Org. Chem. 2000, 65, 3603.
30. [7i] P. Langer, I. Karimé, Synlett 2000, 743.
31. [7j] P. Langer, V. Köhler, Org. Lett. 2000, 1597.
32. [7k] P. Langer, B. Kracke, Tetrahedron Lett. 2000, 4545.
33. [7l] P. Langer, M. Döring, D. Seyferth, Synlett 1999, 135.
34. [7m] P. Langer, M. Döring, Chem. Commun. 1999, 2439.
35. [7n] P. Langer, Chem. Commun. 1999, 1217.
36. [7o] P. Langer, J. Wuckelt, M. Döring, R. Beckert, Eur. J. Org. Chem. 1998, 1467.
37. [7p] P. Langer, M. Döring, D. Seyferth, Chem. Commun. 1998, 1927.
38. [7q] P. Langer, M. Döring, Synlett 1998, 396.
39. [7r] P. Langer, M. Döring, Synlett 1998, 399.
40. [8a] P. Langer, M. Stoll, Angew. Chem. 1999, 111, 1919;
41. Angew. Chem. Int. Ed. 1999, 38, 1803.
42. [8b] P. Langer, T. Schneider, M. Stoll, Chem. Eur. J. 2000, 6, 3204.
43. [8c] P. Langer, T. Eckardt, Synlett 2000, 844.
44. [8d] P. Langer, N. N. R. Saleh, Org. Lett. 2000, 3333.
45. D. Lindauer, R. Beckert, M. Döring, P. Fehling, H. Görls, J. Prakt. Chem. 1995, 337, 143.
46. 1H-Pyrrolo[1,2-a]benzimidazol-1-ones have previously been prepared by a different approach: W. Ried, H. Knorr, Justus Liebigs Ann. Chem. 1976, 284.
47. [11a] For tne preparation of a 2-hydroxy-1H-imidazo[1,2-a]imidazol-1-one, see: M. Smionar, Chem. Heterocycl. Compd. (Engl. Transl.) 1976, 12, 115.
48. [13b]
49. S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, K. Tanabe, J. Am. Chem. Soc. 2000, 3746.
50. For related compounds, see: [13a] R. Beckert, M. Gruner, J. Prakt. Chem. 1992, 334, 611.
51. [13b] A. K. El-Shafei, H. S. Kashef, A.-B. A. G. Ghattas, Gazz. Chim. Ital 1981, 111, 409.
52. Only a very few bicyclic systems related to 12a-d have been reported previously: [14a] C. K. Ingold, S. D. Weaver, J. Chem. Soc. 1925, 127, 378.
53. For the spectroscopic data of 1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-one, see: [14b] H. Quast, S. Ivanova, E.-M. Peters, K. Peters, H. G. von Schnering, Liebigs Ann. 1996, 1541.
54. [14c] For hericenes, see: P. Vogel, in Theoretically interesting Molecules, vol. 1 (Ed.: R. P. Thummel), JAI Press, Greenwich, CT, USA, 1989, p. 201.
55. M. S. Ashwood, A. W. Gibson, P. G. Houghton, G. R. Humphrey, D. C. Roberts, S. H. B. Wright, J. Chem. Soc., Perkin Trans. 1 1995, 641.
56. M. Kato, S. Nishino, K. Ito, H. Yamakuni, H. Takasugi, Chem. Pharm. Bull. 1995, 43, 1358.
57. R. M. Snider, Science 1991, 251, 435.
58. H. M. R. Hoffmann, J. Rabe, Angew. Chem. 1983, 95, 795;
59. Angew. Chem. Int. Ed. Engl. 1983, 22, 795.
60. [19a] R. Gompper, H.-U. Wagner, Angew. Chem. Int. Ed. Engl. 1988, 27, 1437.
61. [19b] F. Effenberger, H. Schlosser, P. Bäuerle, S. Maier, H. Port, H. C. Wolf, Angew. Chem. Int. Ed. Engl. 1988, 27, 281.
62. [19c] J. Fabian, H. Nakazumi, M. Matsuoka, Chem. Rev. 1992, 92, 1197.
63. [19d] Z. Riedl, G. Hajós, A. Messmer, A. Rockenbauer, L. Korecz, G. Kollenz, W. M. F. Fabian, K. Peters, E.-M. Peters, Chem. Commun. 1997, 757.
64. Further details of the crystal structure investigations are available on requests from the Cambridge Crystallographic Data Centre CCDC (12 Union Road, Cambridge CB2 1EZ, UK), on quoting the depository numbers CSD-132364 (6c), -132365 (7a), -132366 (8b), the names of the authors, and the journal citation.
65. MOLEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, The Netherlands, 1990.
66. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467.
67. G. M. Sheldrick, University of Göttingen, Germany, 1993.
68. J. J. P. Stewart, "AMI", in The Encyclopedia of Computational Chemistry (Eds.: P. v. R. Schleyer, N. L. Allinger, T. Clark, J. Gasteiger, P. Kollman, H. F. Schaefer III, P. R. Schreiner), John Wiley & Sons, Chichester, 1998, pp. 2574.
69. J. A. Pople et al., Gaussian 98, Revision A.5, Gaussian, Inc., Pittsburgh PA, 1998.