One-pot synthesis of tri- And tetrasubstituted pyridines by sequential ring-opening/cyclization/oxidation of N-arylmethyl 3-aziridinylpropiolate esters

Angewandte Chemie - International Edition

Volumn 53, Issue 52, 2014, Pages 14550-14554

  Yoshida, Masahiro ^a   Mizuguchi, Tomotaka ^a   Namba, Kosuke ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Cyclization; Heterocycles; Organocatalysis; Small ring compounds; Synthetic methods

Indexed keywords

CATALYSIS; ESTERIFICATION; ESTERS; PHOSPHORUS COMPOUNDS; PYRIDINE; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DIHYDROPYRIDINES; HETEROCYCLES; NOVEL STRATEGIES; ONE-POT SYNTHESIS; ORGANOCATALYSIS; REACTION CONDITIONS; SMALL RINGS; SYNTHETIC METHODS;

CYCLIZATION;

ESTERS; IMINES; PHOSPHINE; PHOSPHINES; PYRIDINES;

CATALYSIS; CHEMICAL SYNTHESIS; CHEMISTRY; CYCLIZATION; OXIDATION-REDUCTION; STEREOISOMERISM;

CATALYSIS; CYCLIZATION; ESTERS; IMINES; OXIDATION-REDUCTION; PHOSPHINES; PYRIDINES; STEREOISOMERISM;

EID: 84919665429     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409015     Document Type: Article

References (83)

1. a) J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337
2. b) S. D. Roughley, A. M. Jordan, J. Med. Chem. 2011, 54, 3451
3. c) M. Knip, I. F. Douek, W. P. T. Moore, H. A. Gillmor, A. E. M. McLean, P. J. Bingley, E. A. M. Gale, Diabetologia 2000, 43, 1337.
4. a) J. A. Varela, C. Saa, Chem. Rev. 2003, 103, 3787
5. b) G. D. Henry, Tetrahedron 2004, 60, 6043
6. c) G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644
7. d) B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085
8. e) B. Groenendaal, E. Ruijter, R. V. A. Orru, Chem. Commun. 2008, 5474
9. f) M. D. Hill, Chem. Eur. J. 2010, 16, 12052
10. K.Kral, M.Hapke, Angew. Chem. Int. Ed. 2011, 50, 2434;
11. Angew. Chem. 2011, 123, 2482;
12. h) J. A. Bull, J. J. Mousseau, G. Pelletier, A. B. Charette, Chem. Rev. 2012, 112, 2642.
13. a) T. Sakai, R. L. Danheiser, J. Am. Chem. Soc. 2010, 132, 13203
14. b) I. Nakamura, D. Zhang, M. Terada, J. Am. Chem. Soc. 2010, 132, 7884
15. C.Wang, X.Li, F.Wu, B.Wan, Angew. Chem. Int. Ed. 2011, 50, 7162;
16. Angew. Chem. 2011, 123, 7300
17. d) M. Ohashi, I. Takeda, M. Ikawa, S. Ogoshi, J. Am. Chem. Soc. 2011, 133, 18018
18. e) D. S. Kim, J. W. Park, C. H. Jun, Chem. Commun. 2012, 48, 11334
19. )W. Gati, M. M. Rammah, M. B. Rammah, F. Couty, G. Evano, J. Am. Chem. Soc. 2012, 134, 9078
20. g) S. Yamamoto, K. Okamoto, M. Murakoso, Y. Kuninobu, K. Takai, Org. Lett. 2012, 14, 3182;
21. h) Y. Wei, N. Yoshikai, J. Am. Chem. Soc. 2013, 135, 3756; for examples about the synthesis from aziridines
22. N. S. Y. Loy A. Singh X. Xu C.-M. Park Angew. Chem. Int. Ed. 2013 52 2212
23. i) N. S. Y. Loy, A. Singh, X. Xu, C.-M. Park, Angew. Chem. Int. Ed. 2013, 52, 2212; Angew. Chem. 2013, 125, 2268
24. j) A. Padwa, P. H. J. Carlsen, Tetrahedron Lett. 1978, 19, 433
25. k) Y. Jiang, C.-M. Park, T.-P. Loh, Org. Lett. 2014, 16, 3432
26. A. Prechter G. Henrion P. Faudot dit Bel F. Gagosz Angew. Chem. Int. Ed. 2014 53 4959
27. l) A. Prechter, G. Henrion, P. Faudot dit Bel, F. Gagosz, Angew. Chem. Int. Ed. 2014, 53, 4959; Angew. Chem. 2014, 126, 5059;
28. m) J. C. Adrian, Jr., L. Hassib, N. De Kimpe, M. Keppens, Tetrahedron 1998, 54, 2365
29. )W. Aelterman, N. De Kimpe, V. Tyvorskii, O. Kulinkovich, J. Org. Chem. 2001, 66, 53
30. D. Reg-s, M. M. Afonso, J. A. Palenzuela, Tetrahedron 2012, 68, 9345.
31. A. K. Yudin, Aziridines and Epoxides in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
32. a) X. E. Hu, Tetrahedron 2004, 60, 2701
33. b) P. Lu, Tetrahedron 2010, 66, 2549
34. c) S. H. Krake, S. C. Bergmeier, Tetrahedron 2010, 66, 7337
35. d) S. Stanković, M. D'hooghe, S. Catak, H. Eum, M. Waroquier, V. Van Speybroeck, N. De Kimpe, H.-J. Ha, Chem. Soc. Rev. 2012, 41, 643.
36. a) F. Chemla, F. Ferreira, Curr. Org. Chem. 2002, 6, 539
37. b) H. Ohno, Chem. Rev. 2014, 114, 7784.
38. a) P.W. Davies, N. Martin, Org. Lett. 2009, 11, 2293
39. b) P.W. Davies, N. Martin, J. Organomet. Chem. 2011, 696, 159
40. c) D.-D. Chen, X.-L. Hou, L.-X. Dai, Tetrahedron Lett. 2009, 50, 6944
41. d) X. Du, X. Xie, Y. Liu, J. Org. Chem. 2010, 75, 510
42. e) A. Blanc, A. Alix, J.-M. Weibel, P. Pale, Eur. J. Org. Chem. 2010, 1644
43. f) M. Yoshida, M. Al-Amin, K. Shishido, Synthesis 2009, 2454
44. g) M. Yoshida, M. Al-Amin, K. Shishido, Tetrahedron Lett. 2009, 50, 6268
45. h) M. Yoshida, Y. Maeyama, M. Al-Amin, K. Shishido, J. Org. Chem. 2011, 76, 5813
46. i) M. Yoshida, S. Easmin, M. Al-Amin, Y. Hirai, K. Shishido, Tetrahedron 2011, 67, 3194
47. j) A. Okano, S. Oishi, T. Tanaka, N. Fujii, H. Ohno, J. Org. Chem. 2010, 75, 3396
48. k) N. Kern, A. Blanc, J.-M.Weibel, P. Pale, Chem. Commun. 2011, 47, 6665
49. l) N. Kern, A. Blanc, S. Miaskiewicz, M. Robinette, J.-M. Weibel, P. Pale, J. Org. Chem. 2012, 77, 4323.
50. Z. He, A. K. Yudin, Angew. Chem. Int. Ed. 2010, 49, 1607;
51. Angew. Chem. 2010, 122, 1651
52. b) Z. He, D. Dobrovolsky, P. Trinchera, A. K. Yudin, Org. Lett. 2013, 15, 334.
53. a) H. Ohno, A. Toda, Y. Takemoto, N. Fujii, T. Ibuka, J. Chem. Soc. Perkin Trans. 1 1999, 2949
54. b) H. Ohno, A. Toda, N. Fujii, Y. Takemoto, T. Tanaka, T. Ibuka, Tetrahedron 2000, 56, 2811.
55. a) D. Borel, Y. Gelas-Mialhe, R. Vessière, Can. J. Chem. 1976, 54, 1590
56. b) J. Åhman, P. Somfai,D. Tanner, J. Chem. Soc. Chem. Commun. 1994, 2785
57. c) J. Åhman, P. Somfai, Tetrahedron Lett. 1995, 36, 1953
58. d) J. Åhman, P. Somfai, Tetrahedron 1999, 55, 11595.
59. a) G. Sirasani, R. B. Andrade, Org. Lett. 2009, 11, 2085;
60. b) G. Sirasani, T. Paul, W. Dougherty, Jr., S. Kassel, R. B. Andrade, J. Org. Chem. 2010, 75, 3529
61. c) G. Sirasani, R. B. Andrade, Org. Lett. 2011, 13, 4736.
62. a) X.-F. Zhu, C. E. Henry, O. Kwon, Tetrahedron 2005, 61, 6276
63. b) Y.-L. Shi, M. Shi, Org. Lett. 2005, 7, 3057;
64. c) G.-L. Zhao, M. Shi, J. Org. Chem. 2005, 70, 9975
65. d) L. Jean, A. Marinetti, Tetrahedron Lett. 2006, 47, 2141
66. e) A. Scherer, J. A. Gladysz, Tetrahedron Lett. 2006, 47, 6335
67. f) X. Tang, B. Zhang, Z. He, R. Gao, Z. He, Adv. Synth. Catal. 2007, 349, 2007;
68. N. Fleury-Br-geot, L. Jean, P. Retailleau, A. Marinetti, Tetrahedron 2007, 63, 11920
69. h) A. Panossian, N. Fleury-Br-geot, A. Marinetti Eur. J. Org. Chem. 2008 3826 A. Marinetti, Eur. J. Org. Chem. 2008, 3826
70. i) Y.-Q. Fang, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 5660
71. j) L.-G. Meng, P. Cai,Q. Guo, S. Xue, J. Org. Chem. 2008, 73, 8491
72. B.Zhang, Z.He, S.Xu, G.Wu, Z.He, Tetrahedron 2008, 64, 9471
73. N. Pinto, N. Fleury-Br-geot, A. Marinetti, Eur. J. Org. Chem. 2009, 146;
74. m) X.-Y. Guan, M. Shi, J. Org. Chem. 2009, 74, 1977
75. n) M. Schuler, D. Duvvuru, P. Retailleau, J.-F. Betzer, A. Marinetti, Org. Lett. 2009, 11, 4406
76. X.Han, F.Zhong, Y.Wang, Y.Lu, Angew. Chem. Int. Ed. 2012, 51, 767;
77. Angew. Chem. 2012, 124, 791
78. p) X.-Y. Chen, R.-C. Lin, S. Ye, Chem. Commun. 2012, 48, 1317
79. q) Y.-Q. Wang, Y. Zhang, H. Dong, J. Zhang, J. Zhao, Eur. J. Org. Chem. 2013, 3764
80. r) L.-J. Yang, S. Wang, J. Nie, S. Li, J.- A. Ma, Org. Lett. 2013, 15, 5214.
81. a) E. Leete, J. Am. Chem. Soc. 1961, 83, 3645
82. b) H. Uno, S. Okada, Y. Shiraishi, K. Shimokawa, H. Suzuki, Chem. Lett. 1988, 1165
83. c) D. M. McKinnon, A. Abouzeid, J. Heterocycl. Chem. 1991, 28, 347.