Synthesis of multisubstituted 1H-pyrrole: Selenium-catalyzed reaction of γ-nitro substituted carbonyl compounds and carbon monoxide

Tetrahedron

Volumn 70, Issue 29, 2014, Pages 4395-4399

  Umeda, Rui ^a   Mashino, Tsukasa ^a   Nishiyama, Yutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

Carbon monoxide; Pyrrole; Selenium; Nitro substituted carbonyl compound

Indexed keywords

CARBON MONOXIDE; CARBONYL DERIVATIVE; PYRROLE; SELENIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 84901695922     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.04.061     Document Type: Article

References (80)

1. R.A. Jones Pyrroles Part II 1992 Wiley New York, NY
2. H. Fan, J.N. Peng, M.T. Hamann, and J.F. Hu Chem. Rev. 108 2008 264
3. A. Grube, and M. Kock Org. Lett. 8 2006 4675
4. A. Furstner Angew. Chem., Int. Ed. 42 2003 3582
5. M. Fujita, Y. Nakao, S. Matsunaga, M. Seiki, Y. Itoh, J. Yamashita, R.W.M. Von Soest, and N. Fusetani J. Am. Chem. Soc. 125 2003 15700
6. D.L. Boger, C.W. Boyce, M.A. Labroli, C.A. Sehon, and Q. Jin J. Am. Chem. Soc. 121 1999 54 and references therein
7. L. Weber Curr. Med. Chem. 9 2002 2085
8. C. Hulme, and V. Core Curr. Med. Chem. 10 2003 51
9. B.D. Roth Prog. Med. Chem. 40 2002 1
10. B.B. Lohaya, and V. Lohyah Pure Appl. Chem. 77 2005 179
11. P. Dydio, D. Lichosyt, and J.J. Jurczak Chem. Soc. Rev. 40 2011 2971
12. Y.-Z. Long, M.-M. Li, C. Gu, M. Wan, J.-L. Duvail, Z. Liu, and Z. Fan Prog. Polym. Sci. 36 2011 1415
13. S.K. Kim, and J.L. Sessler Chem. Soc. Rev. 39 2010 3784
14. A. Berlin, B. Vercelli, and G. Zotti Polym. Rev. 48 2008 493
15. S. Gabriel, M. Cecius, K. Fleury-Frenette, D. Cossement, M. Heeq, N. Ruth, R. Jerone, and C. Jerome Chem. Mater. 19 2007 2364
16. S.J. Higgins Chem. Soc. Rev. 26 1997 247
17. P. Novak, K. Muller, K. Si, V. Santhanam, and O. Haac Chem. Rev. 97 1997 207
18. J. Bergman, and T. Janosik A.R. Katritzky, C.A. Ramsden, F.F.V. Scriven, R.J.K. Taylor, Comprehensive Heterocyclic Chemistry III Vol. 3 2008 Elsevier Oxford, UK 219
19. G.B. Jones, and B.J. Chapman A.R. Katritzky, C.W. Rees, E.F.V. Scriven, C.W. Bird, Comprehensive Heterocyclic Chemistry II Vol. 2 1996 Pergamon Oxford, UK 1
20. G.B. Jones, and B.J. Chapman A.R. Katritzky, C.W. Rees, E.F.V. Scriven, C.W. Bird, Comprehensive Heterocyclic Chemistry II Vol. 2 1996 Pergamon Oxford, UK 119
21. V. Estevez, M. Vilacampa, and J.C. Menendez Chem. Soc. Rev. 39 2010 4402
22. F. Belina, and R. Rossi Tetrahedron 62 2006 7213
23. V.F. Ferreira, M.C.B.V. de Souza, A.C. Cunha, L.O.R. Pereira, and M.L.G. Ferreira Org. Prep. Proced. Int. 33 2001 411
24. R.J. Billedeau, K.R. Klein, D. Kaplan, and Y. Lou Org. Lett. 15 2013 1424
25. L. Meng, K. Wu, C. Liu, and A. Lei Chem. Commun. 2013 5853
26. C.-Q. Ren, C.-H. Di, Y.-L. Zhan, and J.P. Zhang Tetrahedron Lett. 54 2013 1478
27. B. Li, N. Wang, Y. Liang, S. Xu, and B. Wang Org. Lett. 15 2013 136
28. X. Qi, X. Xu, and C.M. Park Chem. Commun. 2012 3996
29. F. Chen, T. Shen, Y. Cui, and N. Jian Org. Lett. 14 2012 4926
30. B.B. Thompson, and J. Montgomery Org. Lett. 13 2011 3289
31. S. Rakshit, F.W. Patureau, and F. Glorius J. Am. Chem. Soc. 132 2010 9585
32. D. Ciez Org. Lett. 11 2009 4282
33. S. Chiba, Y.-F. Wang, G. Lapointe, and K. Narasaka Org. Lett. 10 2008 313
34. M. Shindo, Y. Yoshimura, M. Hayashi, H. Soejima, T. Yoshikawa, K. Matsumoto, and K. Shishido Org. Lett. 9 2007 1963
35. D.J. St Cyr, and B.A. Arndtsen J. Am. Chem. Soc. 129 2007 12366
36. C. Schmuck, and D. Rupprecht Synthesis 2007 3095 3110
37. X. Wan, D. Xing, Z. Fang, B. Li, F. Zhao, K. Zhang, L. Yang, and Z. Shi J. Am. Chem. Soc. 128 2006 12046 and references therein
38. R. Umeda, Y. Nishimoto, T. Mashino, and Y. Nishiyama Heterocycles 57 2013 1249
39. R. Umeda, S. Morishita, and Y. Nishiyama Heteroat. Chem. 22 2011 571
40. Y. Nishiyama, M. Fujimoto, and N. Sonoda Synlett 2006 109
41. Y. Nishiyama, Y. Naito, and N. Sonoda Synlett 2004 886
42. Y. Nishiyama, M. Hirose, W. Kitagaito, and N. Sonoda Tetrahedron Lett. 43 2002 1855
43. Y. Nishiyama, R. Maema, K. Ohno, M. Hirose, and N. Sonoda Tetrahedron Lett. 40 1999 5717
44. X. Zhang, P. Wang, D. Li, B. Liang, and Q. Wang Huaxue Tongbao 75 2012 368
45. X. Zhang, and H. Jing J. Mol. Catal. A Chem. 302 2009 137
46. X. Liu, and S. Lu J. Mol. Catal. A Chem. 300 2009 36
47. X. Zhang, H. Jing, J. Miao, and S. Lu Huaxue Jinzhan 20 2008 1102
48. X.-P. Zhang, and S.-W. Lu J. Chem. Res. 2008 589
49. X. Wang, P. Li, X. Yuan, and S. Lu J. Mol. Catal. A Chem. 253 2006 261
50. X. Liu, and S. Lu Cuihua Xuebao 26 2005 74
51. X. Wang, G. Ling, Y. Xue, and S. Lu Eur. J. Org. Chem. 26 2005 74
52. H. Zhang, and S. Lu Synthesis 2005 1535
53. J. Chen, G. Ling, Z. Yu, S. Wu, X. Zhao, X. Wu, and S. Lu Adv. Synth. Catal. 346 2004 1267
54. X. Wang, S. Lu, and Z. Yu Adv. Synth. Catal. 346 2004 929
55. X. Liu, Q. Liu, and S. Lu Cuihua Xuebao 25 2004 597
56. X. Liu, and S. Lu J. Mol. Catal. A Chem. 212 2004 127
57. X. Liu, A. Peng, and S. Lu Cuihua Xuebao 24 2003 731
58. J. Mei, and S. Lu Cuihua Xuebao 24 2003 321
59. J. Chen, G. Ling, and S. Lu Tetrahedron 59 2003 8251
60. J. Mei, and S. Lu Huaxue Jinzhan 14 2002 433
61. Y. Xue, and S. Lu Cuihua Xuebao 22 2001 387
62. Y. Yang, and S. Lu Cuihua Xuebao 20 1999 224
63. Y. Yang, and S. Lu Tetrahedron Lett. 40 1999 4845
64. Barton et al. have reported the synthesis of pyrroles by the reaction of γ-nitro substituted ketones with diphenyl disulfide and triphenylphosphine. See: D.H.R. Barton, W.B. Mortherwell, E.S. Simon, and S.Z. Zard J. Chem. Soc., Perkin Trans. 1 1986 2243
65. Formamidinesulfinic acid and triethylamine were useful reagents on the conversion of γ-nitro substituted ketones bearing an electron-withdrawing group germinal to the nitro moiety to the corresponding pyrroles. See: B. Quiclet-Sire, I. Thevenot, and S.Z. Zard Tetrahedron Lett. 36 1995 9469
66. It seems that compound 5a was formed by the selective reduction of the carbon-carbon double bond of chalcone, which was generated in situ by the retro-Michael reaction of 1a, under the reaction condition. Indeed, the carbon-carbon double bond of α,β-unsaturated carbonyl compounds can be selectively reduced under Se-CO reaction system. See: Y. Nishiyama, Y. Makino, S. Hamanaka, A. Ogawa, and N. Sonoda Bull. Chem. Soc. Jpn. 62 1989 1682 1684
67. K. Kondo, S. Yokoyama, N. Miyoshi, S. Murai, and N. Sonoda Angew. Chem., Int. Ed. Engl. 18 1979 691
68. We recently reported that aliphatic nitro compounds were reduced by carbon monoxide in the presence of selenium catalyst to give the corresponding oximes in moderate to good yields. See: Y. Nishiyama, S. Ikeda, H. Nishida, and R. Umeda Bull. Chem. Soc. Jpn. 83 2010 816
69. N. Sonoda, K. Kondo, K. Nagano, N. Kambe, and F. Morimoto Angew. Chem., Int. Ed. Engl. 19 1980 308
70. T. Miyata, K. Kondo, S. Murai, T. Hirashima, and N. Sonoda Angew. Chem., Int. Ed. Engl. 19 1980 1008
71. W. Zhao, and M.F. Carreira Chem. - Eur. J. 12 2006 7254
72. M.J. Hell, S.O. McDonne3ll, J. Killoran, and D.F. O'Shea J. Org. Chem. 70 2005 5571
73. S. Kiren, X. Hong, A.C. Leverett, and A. Padwa Org. Lett. 11 2009 1233
74. H.A. Houwing, and A.M. Van Lensen J. Heterocycl. Chem. 18 1981 1127
75. P. Chiu, and M.P. Sammes Tetrahedron 44 1988 3530
76. A. Laurent, P. Mison, A. Nafti, and N. Pellossoer Tetrahedron 35 1979 2285
77. H. Iida, T. Moromuzato, H. Hamana, and K. Matsumoto Tetrahedron Lett. 48 2007 2037
78. D.J. Fox, D.S. Pedersen, and S. Warren Org. Biomol. Chem. 4 2006 3102
79. A.H. Cook, and J.R. Maier J. Chem. Soc. 1944 482
80. X. Liu, L. Huang, F. Zheng, and Z. Zhan Adv. Synth. Catal. 350 2008 2778