Cycloaddition and cyclization chemistry of 2H-azirines

Advances in Heterocyclic Chemistry

Volumn 99, Issue C, 2010, Pages 1-31

  Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84863293105     PISSN: 00652725     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2725(10)09901-0     Document Type: Chapter

References (88)

1. A. L. Logothetis, J. Org. Chem., 29, 3049-3052 (1964).
2. B. Singh and E. F. Ullman, J. Am. Chem. Soc., 89, 6911-6916 (1967).
3. F. P. Woerner, H. Reimlinger, and D. R. Arnold, Angew. Chem. Int. Ed. Engl., 30, 130-131 (1968).
4. V. Nair, J. Org. Chem., 33, 2121-2123 (1968).
5. R. Huisgen, J. Org. Chem., 33, 2291-2297 (1968).
6. K. Isomura, S. Kobayashi, and H. Taniguchi, Tetrahedron Lett., 9, 3499-3502 (1968).
7. A. Hassner, R. J. Isbister, R. B. Greenwald, J. T. Klug, and E. C. Taylor, Tetrahedron, 25, 1637-1641 (1969).
8. T. Nishiwaki, Tetrahedron Lett., 10, 2049-2052 (1969).
9. K. Isomura, M. Okada, and H. Taniguchi, Tetrahedron Lett., 10, 4073-4076 (1969).
10. F. R. Woerner, H. Reimlinger, and R. Merenyi, Chem. Ber., 104, 2789-2792 (1971).
11. D. J. Anderson, T. L. Gilchrist, G. E. Gymer, and C. W. Rees, J. Chem. Soc., Chem. Commun., 1518-1521 (1971).
12. T. Nishiwaki and T. Saito, J. Chem. Soc., 3021-3027 (1971).
13. V. Nair, Tetrahedron Lett., 12, 4831-4833 (1971).
14. A. Padwa, J. Smolanoff, and S. I. Wetmore, Jr., J. Chem. Soc., Chem. Commun., 409-410 (1972).
15. T. Nishiwaki, J. Chem. Soc., Chem. Commun., 565-566 (1972).
16. A. Padwa and E. Glazer, J. Am. Chem. Soc., 94, 7788-7797 (1972).
17. A. Hassner and D. J. Anderson, J. Am. Chem. Soc., 94, 8255-8256 (1972).
18. T. Nishiwaki and F. Fujiyama, J. Chem. Soc., Perkin Trans. 1, 1456-1459 (1972).
19. V. Nair, J. Org. Chem., 37, 802-804 (1972).
20. A. R. Doumaux, J. Org. Chem., 37, 508-510 (1972).
21. H. Diirr and R. Sergio, Tetrahedron Lett., 13, 3479-3482 (1972).
22. N. S. Narasimhan, H. Heimgartner, H. J. Hansen, and H. Schmid, Helv. Chim. Acta, 56, 1351-1370 (1973).
23. A. Padwa, M. Dharan, J. Smolanoff, and S. Wetmore, J. Am. Chem. Soc., 95, 1954-1961 (1973).
24. K. N. Houk, J. Sims, R. E. Duke, R. W. Strozier, and J. K. George, J. Am. Chem. Soc., 95, 7287-7301 (1973).
25. M. J. Haddadin and A. Hassner, J. Org. Chem., 38, 3466-3471 (1973).
26. R. E. Moerck and M. A. Battiste, J. Chem. Soc., Chem. Commun., 782-783 (1974).
27. L. A. Wendling and R. G. Bergman, J. Am. Chem. Soc., 96, 308-309 (1974).
28. A. Hassner and D. J. Anderson, J. Org. Chem., 39, 2031-2036 (1974).
29. D. J. Anderson, A. Hassner, and D. Y. Tang, J. Org. Chem., 39, 3076-3080 (1974).
30. A. Padwa, L. Smolanoff, and A. Tremper, Tetrahedron Lett., 15, 29-32 (1974).
31. G. C. Johnson and R. H. Levin, Tetrahedron Lett., 15, 2303-2306 (1974).
32. A. Padwa and P. H. J. Carlsen, J. Am. Chem. Soc., 97, 3862-3864 (1975).
33. A. Demoulin, H. Gorissen, A.-M. Hesbain-Frisque, and L. Ghosez, J. Am. Chem. Soc., 97, 4409-4410 (1975).
34. A. Padwa, J. Smolanoff, and A. Tremper, J. Am. Chem. Soc., 97, 4682-4700 (1975).
35. A. Padwa and J. K. Rasmussen, J. Am. Chem. Soc., 97, 5912-5914 (1975).
36. V. Nair, J. Heterocycl. Chem., 12, 183-184 (1975).
37. A. Padwa, Acc. Chem. Res., 9, 371-378 (1976).
38. A. Padwa, A. Ku, A. Mazzu, and S. I. Wetmore, J. Am. Chem. Soc., 98, 1048-1050 (1976).
39. A. Padwa and P. H. J. Carlsen, J. Org. Chem., 41, 180-182 (1976).
40. A. Padwa, J. Smolanoff, and A. Tremper, J. Org. Chem., 41, 543-549 (1976).
41. L. A. Wendling and R. G. Bergman, J. Org. Chem., 41, 831-836 (1976).
42. P. Gilgen, H. Heimgartner, H. Schmid, and H. J. Hansen, Heterocycles, 6, 143-152 (1977).
43. H. Taniguchi, K. Isomura, and T. Tanaka, Heterocycles, 6, 1563-1568 (1977).
44. L. Ghosez, A. Demoulin, M. Henriet, E. Sonveaux, M. Van Meerssche, G. Germain, and J.-P. Declercq, Heterocycles, 7, 895-902 (1977).
45. A. Padwa and N. Kamigata, J. Am. Chem. Soc., 99, 1871-1880 (1977).
46. A. Padwa, P. H. J. Carlsen, and A. Tremper, J. Am. Chem. Soc., 100, 4481-4490 (1978).
47. B. Bigot, R. Ponec, A. Sevin, and A. Devaquet, J. Am. Chem. Soc., 100, 6575-6580 (1978).
48. A. Padwa and P. H. J. Carlsen, J. Org. Chem., 43, 2029-2037 (1978).
49. A. Padwa and P. H. J. Carlsen, in "Reactive Intermediates" (R. A. Abramovitch, ed.), Vol. 2, Plenum Press, New York
50. K. Dietliker and H. Heimgartner, Helv. Chim. Acta, 66, 262-295 (1983).
51. V. Nair, in "The Chemistry of Heterocyclic Compounds" (A. Hassner, ed.), Vol. 42, part 1, pp. 215-242, Wiley, New York (1983).
52. A. Padwa and A. D. Woolhouse, in "Comprehensive Heterocyclic Chemistry 1" (A. R. Katritzky and C. W. Rees, eds.), Vol. 7, Pergamon, (1984).
53. A. Hassner, in"Azides and Nitrenes" (E. F. V.Scriven, ed.), pp. 35-51, Academic Press, New York (1984).
54. H.-J. Hansen and H. Heimgartner, in "1,3-Dipolar Cycloaddition Chemistry" (A. Padwa, ed.), Vol. 1, pp. 177-198, Wiley, New York (1984).
55. L. Ghosez, F. Sainte, M. Rivera, C. Bernard-Henriet, and V. Gouverneur, Recl. Trav. Chim. Pays-Bas, 105, 456-461 (1986).
56. M. Saruwatari, K. Isomura, and H. Taniguchi, Heterocycles, 30, 753-758 (1990).
57. H. Heimgartner, Angew. Chem. Int. Ed. Engl., 30, 238-265 (1991).
58. F. Mueller and J. Mattay, Angew. Chem., Int. Ed. Engl., 31, 207-208 (1992).
59. F. Mueller and J. Mattay, Chem. Ber., 126, 543-549 (1993).
60. T. Benincori, E. Brenna, and F. Sannicolo, J. Chem. Soc., Perkin Trans. 1, 675-679 (1993).
61. F. Muller, J. Mattay, and S. Steenken, J. Org. Chem., 58, 4462-4464 (1993).
62. C. B. Bucher, A. Linden, and H. Heimgartner, Helv. Chim. Acta, 78, 935-945 (1995).
63. W. H. Pearson, B. W. Lian, and S. C. Bergmeier, in "Comprehensive Heterocyclic Chemistry 2" (A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, eds.), Vol. 1A, Elsevier, Oxford, UK (1996).
64. V. Piquet, A. Baceiredo, H. Gornitzka, F. Dahan, and G. Bertrand, Chem. Eur. J., 3, 1757-1764 (1997).
65. E. Albrecht, J. Mattay, and S. Steenken, J. Am. Chem. Soc., 119, 11605-11610 (1997).
66. P. Bhullar, T. L. Gilchrist, and P. Maddocks, Synthesis, 271-272 (1997).
67. N. Kanomata and T. Nakata, Heterocycles, 48, 2551-2558 (1998).
68. S. Calvo-Losado, J. J. Quirante, D. Suarez, and T. L. Sordo, J. Comput. Chem., 19, 912-922 (1998).
69. M. J. Alves and T. L. Gilchrist, J. Chem. Soc., Perkin Trans. 1, 299-304 (1998).
70. M. J. Alves and T. L. Gilchrist, Tetrahedron Lett., 39, 7579-7582 (1998).
71. M. J. Alves, J. F. Bickley, and T. L. Gilchrist, J. Chem. Soc., Perkin Trans. 1, 1399-1402 (1999).
72. F. Palacios, E. Herran, and G. Rubiales, J. Org. Chem., 64, 6239-6246 (1999).
73. F. Palacios, A. M. Ochoa de Retana, E. M. de Marigorta, and J. M. de Los Santos, Eur. J. Org. Chem., 2401-2414 (2001).
74. C. A. Ray, E. Risberg, and P. Somfai, Tetrahedron Lett., 42, 9289-9291 (2001).
75. M. J. Alves, N. G. Azoia, J. F. Bickley, A. Gil Fortes, T. L. Gilchrist, and R. Mendonca, J. Chem. Soc., Perkin Trans. 1, 2969-2976 (2001).
76. E. U. Würthwein, T. Hergenröther, and H. Quast, Eur. J. Org. Chem., 1750-1755 (2002).
77. F. Palacios, A. M. Ochoa de Retana, E. M. de Marigorta, and J. M. de Los Santo, Org. Prep. Proc. Int., 34, 219-269 (2002).
78. B. Jousseaume, C. Laporte, T. Toupance, and J. M. Bernar, Tetrahedron Lett., 44, 5983-5985 (2002).
79. A. S. Timén, A. Fischer, and P. Somfai, Chem. Commun., 1150-1151 (2003).
80. A. S. Timén and P. Somfai, J. Org. Chem., 68, 9958-9963 (2003).
81. M. J. Alves, M. M. Duraes, and A. Gil Fortes, Tetrahedron Lett., 44, 5079-5082 (2003).
82. T. M. V. D. Pinho e Melo, A. L. Cardoso, C. S. B. Gomes, and A. M. d'A Rocha Gonsalves, Tetrahedron Lett., 44, 6313-6315 (2003).
83. Y. Yamauchi, T. Kawatee, H. Itahashi, T. Katagiri, and K. Uneyama, Tetrahedron Lett., 44, 6319-6322 (2003).
84. M. J. Alves, M. M. Duraes, and A. G. Fortes, Tetrahedron, 60, 6541-6553 (2004).
85. B. C. Hong, A. K. Gupta, M. F. Wu, and J. H. Liao, Tetrahedron Lett., 45, 1663-1666 (2004).
86. H. Inui and S. Murata, J. Am. Chem. Soc., 127, 2628-2636 (2005).
87. M. J. Alves, A. G. Fortes, and C. Martins, Synthesis, 555-558 (2005).
88. M. J. Alves, A. G. Fortes, and F. T. Costa, Tetrahedron, 62, 3095-3102 (2006).