Ring-substitution, enlargement, and contraction by base-induced rearrangements of N-heterocyclic ammonium salts

Heterocycles

Volumn 92, Issue 5, 2016, Pages 793-828

  Tayama, Eiji ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84973911581     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/REV-16-837     Document Type: Article

References (104)

1. T. S. Stevens, E. M. Creighton, A. B. Gordon, and M. MacNicol, J. Chem. Soc., 1928, 3193.
2. B. J. Millard and T. S. Stevens, J. Chem. Soc., 1963, 3397. This type of rearrangement is sometimes called a [2,3] Stevens rearrangement.
3. M. Sommelet, C. R. Hebd. Seances Acad. Sci., 1937, 205, 56.
4. S. W. Kantor and C. R. Hauser, J. Am. Chem. Soc., 1951, 73, 4122.
5. I. E. Markó, 'Comprehensive Organic Synthesis,' Vol. 3, Chap. 3.10, pp. 913-974, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991
6. 'Nitrogen, Oxygen, and Sulfur Ylide Chemistry,' ed. by J. S. Clark, Oxford University Press, Oxford, 2002
7. L. Kürti and B. Czakó, 'Strategic Applications of Named Reactions in Organic Synthesis,' Elsevier, Amsterdam, 2005
8. R. Bach, S. Harthong, and J. Lacour, 'Comprehensive Organic Synthesis, II,' Vol. 3, Chap. 3.20, pp. 992-1037, ed. by P. Knochel and G. A. Molander, Elsevier, 2014.
9. J. A. Vanecko, H. Wan, and F. G. West, Tetrahedron, 2006, 62, 1043
10. J. B. Sweeney, Chem. Soc. Rev., 2009, 38, 1027
11. J. Clayden, M. Donnard, J. Lefranc, and D. J. Tetlow, Chem. Commun., 2011, 47, 4624
12. F. Couty, B. Drouillat, G. Evano, and O. David, Eur. J. Org. Chem., 2013, 2045
13. G. Lahm, J. C. O. Pacheco, and T. Opatz, Synthesis, 2014, 46, 2413.
14. S. H. Pine, 'Organic Reactions,' Vol. 18, Chap. 4, pp. 403-464, John Wiley & Sons, Inc., New York, 1970.
15. E. Tayama, Chem. Rec., 2015, 789.
16. W. D. Ollis, M. Rey, I. O. Sutherland, and G. L. Closs, J. Chem. Soc., Chem. Commun., 1975, 543
17. W. D. Ollis, M. Rey, and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1983, 1009
18. K. Chantrapromma, W. D. Ollis, and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1983, 1049.
19. W. R. Brasen and C. R. Hauser, Org. Synth., 1954, 34, 61.
20. S. Mageswaran, W. D. Ollis, I. O. Sutherland, and Y. Thebtaranonth, J. Chem. Soc. D, 1971, 1494
21. W. D. Ollis, I. O. Sutherland, and Y. Thebtaranonth, J. Chem. Soc., Perkin Trans. 1, 1981, 1963.
22. E. Vedejs, M. J. Arco, and J. M. Renga, Tetrahedron Lett., 1978, 19, 523.
23. S. Mageswaran, W. D. Ollis, and I. O. Sutherland, J. Chem. Soc., Chem. Commun., 1973, 656
24. S. Mageswaran, W. D. Ollis, and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1981, 1953.
25. G. Wittig, H. Tenhaeff, W. Schoch, and G. Koenig, Liebigs Ann. Chem., 1951, 572, 1.
26. E. Vedejs and G. R. Martinez, J. Am. Chem. Soc., 1979, 101, 6452
27. E. Vedejs and F. G. West, Chem. Rev., 1986, 86, 941.
28. R. E. Gawley, Q. Zhang, and S. Campagna, J. Am. Chem. Soc., 1995, 117, 11817.
29. V. K. Aggarwal, G. y. Fang, J. P. H. Charmant, and G. Meek, Org. Lett., 2003, 5, 1757.
30. J. McKenna, Top. Stereochem., 1970, 5, 275.
31. C. R. Dunbar and F. G. West, Can. J. Chem., 2015, 93, 468.
32. Y. Kawazoe and M. Tsuda, Chem. Pherm. Bull., 1967, 15, 1405
33. D. R. Brown, J. McKenna, and J. M. McKenna, J. Chem. Soc. D, 1969, 186
34. R. V. Smith, F. W. Benz, and J. P. Long, Can. J. Chem., 1973, 51, 171.
35. G. Wittig and H. Streib, Liebigs Ann. Chem., 1953, 584, 1.
36. K. W. Glaeske and F. G. West, Org. Lett., 1999, 1, 31.
37. E. Tayama, S. Nanbara, and T. Nakai, Chem. Lett., 2006, 35, 478.
38. L. Palombi, Catal. Commun., 2011, 12, 485.
39. E. Tayama, R. Sato, M. Ito, H. Iwamoto, and E. Hasegawa, Heterocycles, 2013, 87, 381.
40. B. Drouillat, E. d'Aboville, F. Bourdreux, and F. Couty, Eur. J. Org. Chem., 2014, 1103.
41. J. C. O. Pacheco, G. Lahm, and T. Opatz, J. Org. Chem., 2013, 78, 4985.
42. M. Valpuesta, A. Diaz, R. Suau, and G. Torres, Eur. J. Org. Chem., 2004, 4313.
43. M. Valpuesta, M. Ariza, A. Diaz, G. Torres, and R. Suau, Eur. J. Org. Chem., 2010, 638.
44. M. Valpuesta, M. Ariza, A, Díaz, and R. Suau, Eur. J. Org. Chem., 2010, 4393.
45. S. Mageswaran, W. D. Ollis, D. A. Southam, I. O. Sutherland, and Y. Thebtaranonth, J. Chem. Soc., Perkin Trans. 1, 1981, 1969.
46. A. P. A. Arboré, D. J. Cane-Honeysett, I. Coldham, and M. L. Middleton, Synlett, 2000, 236.
47. S. C. Smith and P. D. Bentley, Tetrahedron Lett., 2002, 43, 899.
48. E. F. Duran-Lara, N. Shankaraiah, D. Geraldo, and L. S. Santos, J. Braz. Chem. Soc., 2009, 20, 813.
49. E. Tayama, H. Tanaka, and T. Nakai, Heterocycles, 2005, 66, 95.
50. B. Drouillat, F. Couty, and J. Marrot, Synlett, 2009, 767.
51. S. Hanessian, C. Talbot, and P. Saravanan, Synthesis, 2006, 723.
52. W.-D. Z. Li and Y.-Q. Wang, Org. Lett., 2003, 5, 2931.
53. M. Sun, H. Lu, Y. Wang, H. Yang, and H. Liu, J. Org. Chem., 2009, 74, 2213.
54. E. Tayama and H. Kimura, Angew. Chem. Int. Ed., 2007, 46, 8869.
55. R. Chicharro, S. de Castro, J. L. Reino, and V. J. Arán, Eur. J. Org. Chem., 2003, 2314.
56. G. S. Gimranova, S. A. Soldatova, A. T. Soldatenkov, and K. B. Polyanskii, Russ. J. Org. Chem., 2008, 44, 750.
57. M. Ariza, A. Díaz, R. Suau, and M. Valpuesta, Eur. J. Org. Chem., 2011, 6507.
58. A. Kowalkowska and A. Jończyk, Tetrahedron, 2015, 71, 9630.
59. S. A. Soldatova, S. V. Akbulatov, G. S. Gimranova, Y. O. Rudakov, K. B. Polyanskii, and A. T. Soldatenkov, Chem. Heterocycl. Compd., 2005, 41, 681
60. S. A. Soldatova, G. S. Gimranova, Z. A. Mamyrbekova, K. B. Polyanskii, S. V. Akbulatov, A. T. Soldatenkov, Chem. Heterocycl. Compd., 2007, 43, 1420.
61. R. Pedrosa, C. Andrés, and M. Delgado, Synlett, 2000, 893.
62. F. Couty, F. Durrat, G. Evano, and D. Prim, Tetrahedron Lett., 2004, 45, 7525.
63. E. Vedejs, J. P. Hagen, B. L. Roach, and K. L. Spear, J. Org. Chem., 1978, 43, 1185.
64. F. Couty, F. Durrat, G. Evano, and J. Marrot, Eur. J. Org. Chem., 2006, 4214.
65. J. C. O. Pacheco and T. Opatz, J. Org. Chem., 2014, 79, 5182.
66. A. Jończyk, D. Lipiak, and K. Sienkiewicz, Synlett, 1991, 493
67. A. Jończyk and D. Lipiak, J. Org. Chem., 1991, 56, 6933
68. T. Zdrojewski and A. Jończyk, Tetrahedron Lett., 1995, 36, 1355.
69. R. W. Jemison, T. Laird, W. D. Ollis, and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1980, 1436.
70. D. Lednicer and C. R. Hauser, J. Am. Chem. Soc., 1957, 79, 4449.
71. M. Nakano and Y. Sato, J. Chem. Soc., Chem. Commun., 1985, 1684.
72. N. Shirai, F. Sumiya, Y. Sato, and M. Hori, J. Chem. Soc., Chem. Commun., 1988, 370
73. N. Shirai, F. Sumiya, Y. Sato, and M. Hori, J. Org. Chem., 1989, 54, 836.
74. F. Sumiya, N. Shirai, and Y. Sato, Chem. Pharm. Bull., 1991, 39, 36
75. T. Kitano, N. Shirai, and Y. Sato, Synthesis, 1991, 996
76. T. Kitano, N. Shirai, and Y. Sato, Chem. Pharm. Bull., 1992, 40, 768
77. T. Kitano, N. Shirai, M. Motoi, and Y. Sato, J. Chem. Soc., Perkin Trans. 1, 1992, 2851
78. Y. Sato, N. Shirai, Y. Machida, E. Ito, T. Yasui, Y. Kurono, and K. Hatano, J. Org. Chem., 1992, 57, 6711
79. A. Sakuragi, N. Shirai, Y. Sato, Y. Kurono, and K. Hatano, J. Org. Chem., 1994, 59, 148
80. N. Kawanishi, N. Shirai, Y. Sato, K. Hatano, and Y. Kurono, J. Org. Chem., 1995, 60, 4272
81. K. Narita, N. Shirai, and Y. Sato, J. Org. Chem., 1997, 62, 2544.
82. R. Maeda and E. Ohsugi, Chem. Pharm. Bull., 1968, 16, 897.
83. D. J. Hyett, J. B. Sweeney, A. Tavassoli, and J. F. Hayes, Tetrahedron Lett., 1997, 38, 8283.
84. J. B. Sweeney, A. Tavassoli, and J. A. Workman, Tetrahedron, 2006, 62, 11506.
85. J. B. Sweeney, A. Tavassoli, N. B. Carter, and J. F. Hayes, Tetrahedron, 2002, 58, 10113.
86. S. J. Neeson and P. J. Stevenson, Tetrahedron Lett., 1988, 29, 3993.
87. J.-P. Liou and C.-Y. Cheng, Tetrahedron Lett., 2000, 41, 915.
88. S. Hanessian and M. Mauduit, Angew. Chem. Int. Ed., 2001, 40, 3810
89. S. Hanessian, S. Parthasarathy, M. Mauduit, and K. Payza, J. Med. Chem., 2003, 46, 34.
90. T. H. West, D. S. B. Daniels, A. M. Z. Slawin, and A. D. Smith, J. Am. Chem. Soc., 2014, 136, 4476.
91. C. Vogel, Synthesis, 1997, 497.
92. J. C. Anderson, J. M. A. O'Loughlin, and J. A. Tornos, Org. Biomol. Chem., 2005, 3, 2741
93. J. C. Anderson, J. G. Ford, and M. Whiting, Org. Biomol. Chem., 2005, 3, 3734
94. P. Somfai and O. Panknin, Synlett, 2007, 1190
95. J. C. Anderson and E. A. Davies, Tetrahedron, 2010, 66, 6300
96. B. Drouillat, K. Wright, P. Quinodoz, J. Marrot, and F. Couty, J. Org. Chem., 2015, 80, 6936.
97. Y. Murata and T. Nakai, Chem. Lett., 1990, 2069
98. I. Coldham, M. L. Middleton, and P. L. Taylor, J. Chem. Soc., Perkin Trans. 1, 1998, 2817
99. J. Blid and P. Somfai, Tetrahedron Lett., 2003, 44, 3159
100. J. Blid, P. Brandt, and P. Somfai, J. Org. Chem., 2004, 69, 3043
101. P. Tuzina and P. Somfai, Tetrahedron Lett., 2007, 48, 4947
102. J. Blid, O. Panknin, P. Tuzina, and P. Somfai, J. Org. Chem., 2007, 72, 1294
103. P. Tuzina and P. Somfai, Org. Lett., 2009, 11, 919
104. R. K. Everett and J. P. Wolfe, J. Org. Chem., 2015, 80, 9041.