Haval-Argade contrathermodynamic rearrangement of alkylidenesuccinimides to alkylmaleimides via the corresponding isoimides: A general approach to alkyl and dialkyl substituted maleimides

Tetrahedron

Volumn 62, Issue 15, 2006, Pages 3557-3563

  Haval, Kishan P ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Alkyl and dialkylmaleimides; Contrathermodynamic rearrangement; Isomaleimides; Maleimides; Wittig coupling

Indexed keywords

ALDEHYDE; ALKYL GROUP; CARBON; CHLORIDE; CYANURIC ACID; EXOCYCLIC DOUBLE BOND; IMIDE; MALEIMIDE; MALEIMIDE DERIVATIVE; SUCCINIMIDE DERIVATIVE;

ARTICLE; CHEMICAL BOND; HYDROLYSIS; KINETICS; POLYMERIZATION; PRIORITY JOURNAL; SUBSTITUTION REACTION; THERMODYNAMICS; WITTIG REACTION;

EID: 33645010415     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.091     Document Type: Article

References (85)

1. L.H. Fleet, and W.H. Gardner Maleic Anhydride Derivatives 1952 Wiley New York
2. D.R. Gedge, and G.J. Pattenden J. Chem. Soc., Chem. Commun. 1978 880
3. B.C. Trivedi, and B.M. Culberston Maleic Anhydride 1982 Plenum New York
4. A.G.M. Barrett, H.B. Broughton, S.V. Attwood, and A.A.L. Gunatilaka J. Org. Chem. 51 1986 495
5. M.E. Baumann, H. Bosshard, W. Breitenstein, and G. Rist Helv. Chim. Acta 69 1986 396
6. V. Balasubramaniyan, and N.P. Argade Tetrahedron 45 1989 835
7. J.D. White, M.P. Dillon, and R.J. Butlin J. Am. Chem. Soc. 114 1992 9673
8. J.E. Baldwin, A. Beyeler, R.J. Cox, C. Kates, G.J. Pritchard, R.M. Adlington, and D.J. Watkin Tetrahedron 55 1999 7363
9. N. Hucher, A. Daich, and B. Decroix Org. Lett. 2 2000 1201
10. C.A. Mitsos, A.L. Zografos, and O. Igglessi-Markopoulou J. Org. Chem. 65 2000 5852
11. D. Laurenti, C. Santelli-Rouvier, G. Pepe, and M. Santelli J. Org. Chem. 65 2000 6418
12. K.I. Booker-Milburn, L.F. Dudin, C.E. Anson, and S.D. Guile Org. Lett. 3 2001 3005
13. G.A. Sulikowski, W. Liu, F. Agnelli, R.M. Corbett, Z. Luo, and S.J. Hershberger Org. Lett. 4 2002 1451
14. V.B. Birman, and S.J. Danishefsky J. Am. Chem. Soc. 124 2002 2080
15. N.S. Simpkins, and C.D. Gill Org. Lett. 5 2003 535
16. H. Uchida, P.Y. Reddy, S. Nakamura, and T. Toru J. Org. Chem. 68 2003 8736
17. G. Hilt, S. Luers, and K.I. Smolko Org. Lett. 7 2005 251
18. R. Shintani, W.L. Duan, and T. Nagano Angew. Chem., Int. Ed. 44 2005 4611
19. Y. Yamamoto, H. Hayashi, T. Saigoku, and H. Nishiyama J. Am. Chem. Soc. 127 2005 10804
20. A.D. Payne, A.C. Willis, and M.S. Sherburn J. Am. Chem. Soc. 127 2005 12188 and refs. cited therein 1a-t
21. C.L. Yeh, W.T. Colwell, and J.I. DeGraw Tetrahedron Lett. 42 1978 3987
22. G.D. James, G. Pattenden, and S.D. Mills Tetrahedron Lett. 26 1985 3617
23. V. Balasubramaniyan, P. Balasubramaniyan, A.S. Shaikh, and N.P. Argade Indian J. Chem. 28B 1989 123
24. A.M. Deshpande, A.A. Natu, and N.P. Argade Heterocycles 51 1999 2159
25. N. Mase, T. Nishi, Y. Takamori, H. Yoda, and K. Takabe Tetrahedron: Asymmetry 10 1999 4469 and refs. cited therein 2a-e
26. H.F. Mark 3rd ed. Encyclopedia of Polymer Science and Technology Vol. 7 2003 Wiley pp 529-554
27. S.B. Singh, D.L. Zink, J.M. Liesch, M.A. Goetz, R.G. Jenkins, M. Nallin-Omstead, K.C. Silverman, G.F. Bills, R.T. Mosley, J.B. Gibbs, G. Albers-Schonberg, and R.B. Lingham Tetrahedron 49 1993 5917
28. K.C. Nicolaou, M.W. Harter, L. Boulton, and B. Jandeleit Angew. Chem., Int. Ed. 36 1997 1194
29. K.C. Nicolaou, P.S. Baran, Y.L. Zhong, K.C. Fong, Y. He, W.H. Yoon, and H.S. Choi Angew. Chem., Int. Ed. 38 1999 1676
30. S.B. Singh, H. Jayasuriya, K.C. Silverman, C.A. Bonfiglio, J.M. Williamsons, and R.B. Lingham Bioorg. Med. Chem. 8 2000 571
31. K.C. Nicolaou, Y.L. Zhong, P.S. Baran, J. Jung, H.S. Choi, and W.H. Yoon J. Am. Chem. Soc. 124 2002 2202 refs. cited therein 4a-e
32. G. Assante, L. Camarda, L. Merlini, and G. Nasini Gazz. Chim. Ital. 109 1979 151
33. X.C. Cheng, T. Kihara, H. Kusakabe, J. Magae, Y. Kobayashi, R.-P. Fang, Z.-F. Ni, Y.-C. Shen, K. Ko, I. Yamaguchi, and K. Isono J. Antibiot. 40 1987 907
34. X.C. Cheng, M. Ubukata, and K. Isono J. Antibiot. 43 1990 890
35. X.-C. Cheng, M. Ubukata, and K. Isono J. Antibiot. 43 1990 809
36. H. Miyagawa, N. Hamada, M. Sato, and T. Ueno Phytochemistry 36 1994 1319 and refs. cited therein 5a-e
37. H. Oikawa, M. Oikawa, T. Ueno, and A. Ichihara Tetrahedron Lett. 35 1994 4809
38. M. Oikawa, T. Ueno, H. Oikawa, and A. Ichihara J. Org. Chem. 60 1995 5048
39. M.J. Kates, and J.H. Schauble J. Org. Chem. 61 1996 4164
40. E.S. Ratemi, J.M. Dolence, C.D. Poulter, and J.C. Vederas J. Org. Chem. 61 1996 6296
41. J.E. Sheppeck, W. Liu, and A.R. Chamberlin J. Org. Chem. 62 1997 387
42. S.B. Desai, and N.P. Argade J. Org. Chem. 62 1997 4862
43. S. Poigny, M. Guyot, and M. Samadi J. Org. Chem. 63 1998 1342
44. R.M. Slade, and B.P. Branchaud J. Org. Chem. 63 1998 3544
45. A.M. Deshpande, A.A. Natu, and N.P. Argade J. Org. Chem. 63 1998 9557
46. S. Mangaleswaran, and N.P. Argade J. Org. Chem. 66 2001 5259
47. A.M. Deshpande, A.A. Natu, and N.P. Argade Synthesis 2001 702 and refs. cited therein 6a-k
48. R.F. Heck J. Am. Chem. Soc. 94 1972 2712
49. K. Osakada, M.K. Doh, F. Ozawa, and A. Yamamoto Organometallics 9 1990 2197
50. D. Zargarian, and H. Alper Organometallics 10 1991 2914
51. B. Gabriele, M. Costa, G. Salerno, and G.P. Chiusoli J. Chem. Soc., Perkin Trans. 1 1994 83
52. B. Gabriele, M. Costa, G. Salerno, and G.P. Chiusoli J. Chem. Soc., Perkin Trans. 1 1997 147
53. L.G. Bruk, I.V. Oshanina, A.P. Kozlova, O.N. Temkin, and K.Yu. Odintsov Russ. Chem. Bull. 47 1998 1071
54. Y. Sakurai, S. Sakaguchi, and Y. Ishii Tetrahedron Lett. 40 1999 1701
55. B. Gabriele, G. Salerno, M. Costa, and G.P. Chiusoli Chem. Commun. 1999 1381
56. J. Li, G. Li, H. Jiang, and M. Chen Tetrahedron Lett. 42 2001 6923 and refs. cited therein 7a-i
57. E.J. Corey, and J.A. Katzenellenbogen J. Am. Chem. Soc. 91 1969 1851
58. J.F. Normant Synthesis 1972 63
59. R.B. Bates, R.S. Cutler, and R.M. Freeman J. Org. Chem. 42 1977 4162
60. R.M. Adlington, J.E. Baldwin, R.J. Cox, and G.J. Pritchard Synlett 2002 820 and refs. cited therein 8a-d
61. A. Kar, S. Gogoi, and N.P. Argade Tetrahedron 61 2005 5297
62. S. Gogoi, and N.P. Argade Tetrahedron 60 2004 9093
63. M. Mondal, and N.P. Argade Tetrahedron Lett. 45 2004 5693
64. M. Mondal, and N.P. Argade Synlett 2004 1243
65. S.B. Mhaske, and N.P. Argade Tetrahedron 60 2004 3417
66. A. Kar, and N.P. Argade Tetrahedron 59 2003 2991
67. S. Mangaleswaran, and N.P. Argade Synthesis 2002 865
68. S.B. Mhaske, and N.P. Argade J. Org. Chem. 66 2001 9038
69. S. Mangaleswaran, and N.P. Argade J. Chem. Soc., Perkin Trans. 1 2001 1764
70. N.P. Argade, and V. Balasubramaniyan Heterocycles 53 2000 475 and refs. cited therein 9a-j
71. E. Hedaya, and S. Theodoropulos Tetrahedron 24 1968 2241
72. S. Mangaleswaran, and N.P. Argade Synthesis 2003 343
73. E. Taskinen Acta Chem. Scand. B39 1985 779
74. M. Labelle, and D. Gravel Can. J. Chem. 63 1985 1884
75. Y. Ikeda, B.Z. Yin, N. Kato, A. Mori, and H. Takeshita Chem. Lett. 8 1992 1453
76. E. Taskinen, J. Salmela, and K. Haapasaari Struct. Chem. 8 1997 425
77. E. Taskinen Struct. Chem. 12 2001 405 and refs. cited therein 12a-e
78. K.P. Haval, S.B. Mhaske, and N.P. Argade Tetrahedron 62 2006 937
79. Y. Furuya, K. Ishihara, and H. Yamamoto J. Am. Chem. Soc. 127 2005 11240 and refs. cited therein 13a,b
80. P. Gamard, F. Sauriol, N. Benhamou, R.R. Belanger, and T.C. Paulitz J. Antibiot. 50 1997 742
81. A. Furstner, O.R. Thiel, L. Ackermann, H.J. Schanz, and S.P. Nolan J. Org. Chem. 65 2000 2204
82. A. Furstner, and T. Dierkes Org. Lett. 2 2000 2463
83. P. Langer, and N.N.R. Saleh Org. Lett. 2 2000 3333
84. A. Lei, M. He, and X. Zhang J. Am. Chem. Soc. 124 2002 8198
85. W.P. Gallagher, and R.E. Maleczka J. Org. Chem. 68 2003 6775 and refs. cited therein 14a-f