Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6678-6681

  Coffin, Aaron R ^a   Roussell, Michael A ^a   Tserlin, Elina ^a   Pelkey, Erin T ^a  

^a HOBART AND WILLIAM SMITH COLLEGES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXALDEHYDES; LITHIUM ALUMINUM HYDRIDE; REGIOSELECTIVE OXIDATION; WEINREB AMIDES;

ALDEHYDES; HYDRIDES; LITHIUM COMPOUNDS; OXIDATION; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

3 PYRROLIN 2 ONE DERIVATIVE; ACETAMIDE DERIVATIVE; ALKENE; ALUMINUM DERIVATIVE; AMIDE; LITHIUM DERIVATIVE; N METHOXY N METHYL 2 ISOCYANOACETAMIDE; N METHOXY N METHYLPYRROLE 2 CARBOXAMIDE DERIVATIVE; PYRROLE 2 CARBOXALDEHYDE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

AMIDES; CYANIDES; MOLECULAR STRUCTURE; PYRROLES; PYRROLIDINES; STEREOISOMERISM;

EID: 33747381269     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061043m     Document Type: Article

References (72)

1. (a) Barbe, J. M.; Burdet, F.; Espinosa, E.; Gros, C. P.; Guilard, R. J. Porphyrins Phthalocyanines 2003, 7, 365-374.
2. (b) Paolesse, R.; Pandey, R. K.; Forsythe, T. P.; Jacquinod, L.; Gerzevske, K. R.; Nurco, D. J.; Senge, M. O.; Licoccia, S.; Boschi, T.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 3869-3882.
3. Notably, pyrrole-2-carboxaldehydes were utilized as building blocks in the total synthesis of chlorophyll a: Woodward, R. B.; Ayer, W. A.; Beaton, J. M.; Bickelhaupt, F.; Bonnett, R.; Buchschacher, P.; Closs, G. L.; Dutler, H.; Hannah, J.; Hauck, F. P.; Itô, S.; Langemann, A.; Le Goff, E.; Leimgruber, W.; Lwowski, W.; Sauer, J.; Valenta, Z.; Volz, H. Tetrahedron 1990, 46, 7599-7659.
4. Thompson, A.; Dolphin, D. J. Org. Chem. 2000, 65, 7870-7888.
5. (a) Ahmed, R.; Leeper, F. J. Org. Biomol. Chem. 2003, 1, 21-23.
6. (b) De Leon, C. Y.; Ganem, B. Tetrahedron 1997, 53, 7731-7752.
7. (a) Lin, N.-H.; Xia, P.; Kovar, P.; Park, C.; Chen, Z.; Zhang, H.; Rosenberg, S. H.; Sham, H. L. Bioorg. Med. Chem. Lett. 2006, 16, 421-426.
8. (b) Sun, L.; Tran, N.; Liang, C.; Tang, F.; Rice, A.; Schreck, R.; Waltz, K.; Shawver, L. K.; McMahon, G.; Tang, C. J. Med. Chem. 1999, 42, 5120-5130.
9. (a) Woydziak, Z. R.; Boiadjiev, S. E.; Norona, W. S.; McDonagh, A. F.; Lightner, D. A. J. Org. Chem. 2005, 70, 8417-8423.
10. (b) Tu, B.; Ghosh, B.; Lightner, D. A. Tetrahedron 2004, 60, 9017-9029.
11. (c) Chen, Q.; Wang, T.; Zhang, Y.; Wang, Q.; Ma, J. Synth. Commun. 2002, 32, 1031-1040.
12. (d) Jacobi, P. A.; DeSimone, R. W.; Ghosh, I.; Guo, J.; Leung, S. H.; Pippin, D. J. Org. Chem. 2000, 65, 8478-8489.
13. (a) Santos, M. M. M.; Lobo, A. M.; Prabhakar, S.; Marques, M. M. B. Tetrahedron Lett. 2004, 45, 2347-2349.
14. (b) Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1997, 119, 9641-9651.
15. (a) Bai, A. P.; Guo, Z. R.; Hu, W. H.; Shen, F.; Cheng, G. F. Chin. Chem. Lett. 2001, 12, 775-778.
16. (b) Bosch, J.; Roca, T.; Catena, J.-L.; Llorens, O.; Pérez, J.-J.; Lagunas, C.; Fernández, A. G.; Miquel, I.; Fernández-Serrat, A.; Farrerons, C. Bioorg. Med. Chem. Lett. 2000, 10, 1745-1748.
17. Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
18. Recent examples of the use of 2-silyloxypyrroles in synthesis: (a) Brimble, M. A.; Burgess, C.; Halim, R.; Petersson, M.; Ray, J. Tetrahedron 2004, 60, 5751-5758.
19. (b) DeGoey, D. A.; Chen, H.-J.; Flosi, W. J.; Grampovnik, D. J.; Yeung, C. M.; Klein, L. L.; Kempf, D. J. J. Org. Chem. 2002, 67, 5445-5453.
20. (c) Li, W.-R.; Lin, S. T.; Hsu, N.-M.; Chern, M.-S. J. Org. Chem. 2002, 67, 4702-4706.
21. (a) Pal, M.; Swamy, N. K.; Hameed, P. S.; Padakanti, S.; Yeleswarapu, K. R. Tetrahedron 2004, 60, 3987-3997.
22. (b) References 6c, 8a, and 8b.
23. Intramolecular condensation approaches to indolocarbazoles: (a) Trost, B. M.; Krische, M. J.; Berl, V.; Grenzer, E. M. Org. Lett. 2002, 4, 2005-2008.
24. (b) Kobayashi, Y.; Fujimoto, T.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 6501-6502.
25. (c) Eils, S.; Winterfeldt, E. Synthesis 1999, 275-281.
26. (a) Beccali, E. M.; Gelmi, M. L.; Marchesini, A. Tetrahedron 1998, 54, 6909-6918.
27. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024-8025.
28. For the oxidation of α-unsubstituted pyrroles: (a) Xie, M.; Lightner, D. A. Tetrahedron 1993, 49, 2185-2200.
29. (b) Bonnett, R.; Buckley, D. G.; Hamzetash, D. J. Chem. Soc., Perkin Trans. 1 1981, 322-325.
30. (c) Bocchi, V.; Chierici, L.; Gardini, G. P.; Mondelli, R. Tetrahedron 1970, 26, 4073-4082.
31. (a) Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem. 1998, 63, 6053-6058.
32. (b) Link, J. T.; Raghavan, S.; Gallant, M.; Danishefsky, S. J.; Chou, T. C.; Ballas, L. M. J. Am. Chem. Soc. 1996, 118, 2825-2842.
33. (c) Link, J. T.; Danishefsky, S. J. Tetrahedron Lett. 1994, 35, 9135-9138.
34. (d) Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361-8364.
35. de Groot, J. A.; Gorter-La Roy, G. M.; van Koeveringe, J. A.; Lugtenburg, J. Org. Prep. Proc. Int. 1981, 13, 97-101.
36. (a) Katritzky, A. R.; Kunihiko, A. Org. Prep. Proc. Int. 1988, 20, 585-590.
37. (b) Brittain, J. M.; Jones, R. A.; Arques, J. S.; Saliente, T. A. Synth. Commun. 1982, 12, 231-248.
38. Examples of formylations that give mixtures of regioisomeric formylpyrroles: (a) Balasubramanian, T.; Strachan, J.-P.; Boyle, P. D.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7919-7929 (compound 4).
39. (b) Reference 2 (compound 24);
40. (c) Reference 4b (compound 29).
41. This work was initially communicated in part at two conferences: (a) Roussell, M. A.; Pelkey, E. T. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA.; American Chemical Society: Washington, DC, 2002; CHED 200.
42. (b) Tserlin, E.; Pelkey, E. T. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA.; American Chemical Society: Washington, DC, 2002; CHED 215.
43. (c) Coffin, A. R.; Pelkey, E. T. Abstract of Papers, 47th Undergraduate Research Symposium-ACS Rochester Section, Geneva, NY.; American Chemical Society: Washington, DC, 2002.
44. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
45. Pichon-Santander, C.; Scott, I. A. Tetrahedron Lett. 2000, 41, 2825-2829.
46. See also: Hwang, K.-O.; Lightner, D. A. Tetrahedron 1994, 50, 1955-1966.
47. (a) Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587-7598.
48. (b) Ono, N.; Kawamura, H.; Bougauchi, M.; Maruyama, K. Tetrahedron 1990, 46, 7483-7496.
49. Recent applications of the Barton-Zard pyrrole synthesis: (a) Okujima, T.; Komobuchi, N.; Uno, H.; Ono, N. Heterocycles 2006, 67, 255-267.
50. (b) Cillo, C. M.; Lash, T. D. Tetrahedron 2005, 61, 11615-11627.
51. (c) Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664-5667.
52. (d) Reference 6a.
53. Examples of pyrrole Weinreb amides in the literature prepared from the corresponding pyrrole-2-carboxylic acids: (a) Ruiz, J.; Sotomayor, N.; Lete, E. Org. Lett. 2003, 5, 1115-1117.
54. (b) Banwell, M.; Smith, J. Synth. Commun. 2001, 31, 2011-2019.
55. (a) Ballini, R.; Barboni, L.; Giarlo, G. J. Org. Chem. 2004, 69, 6907-6908.
56. (b) Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
57. (c) Kornblum, N.; Larson, H. O.; Blackwood, R. K.; Mooberry, D. D.; Oliveto, E. P.; Graham, G. E. J. Am. Chem. Soc. 1956, 78, 1497-1501.
58. (a) Ballini, R.; Castagnani, R.; Petrini, M. J. Org. Chem. 1992, 57, 2160-2162.
59. (b) Robertson, D. N. J. Org. Chem. 1960, 25, 47-50.
60. (a) Kim, S. W.; Bauer, S. M.; Armstrong, R. W. Tetrahedron Lett. 1998, 39, 6993-6996.
61. (b) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727-1732.
62. (a) Kakiuchi, T.; Kinoshita, H.; Inomata, K. Synlett 1999, 901-904.
63. (b) Kohori, K.; Hashimoto, M.; Kinoshita, H.; Inomata, K. Bull Chem. Soc. Jpn. 1994, 67, 3088-3093.
64. (c) see also refs 6a, 6b.
65. With regard to the reported syntheses of isocyanide 7: (a) Reference 27a utilized Boc-glycine but offered very little experimental details and no yields.
66. (b) Reference 27b utilized Cbz-glycine.
67. Kolhatkar, R. B.; Ghorai, S. K.; George, C.; Reith, M. E. A.; Dutta, A. K. J. Med. Chem. 2003, 46, 2205-2215.
68. See Supporting Information for references regarding known pyrrole-2-carboxaldehydes 2 and known 3-pyrrolin-2-ones 3.
69. Davies, I. W.; Marcoux, J.-F.; Corley, E. G.; Journet, M.; Cai, D.-W.; Palucki, M.; Wu, J.; Larsen, R. D.; Rossen, K.; Pye, P. J.; DiMichele, L.; Dormer, P.; Reider, P. J. J. Org. Chem. 2000, 65, 8415-8420.
70. Ruiz, J.; Ardeo, A.; Ignacio, R.; Sotamayor, N.; Lete, E. Tetrahedron 2005, 61, 3311-3324.
71. Dannhardt, G.; Steindl, L. Arch. Pharm. (Weinheim) 1986, 319, 749-755.
72. Yakushijin, K.; Kozuka, M.; Furukawa, H. Chem. Pharm. Bull. 1980, 28, 2178-2184.