Photoreactions of 1-acetylisatin with alkynes: Regioselectivity in oxetene formation and easy access to 3-alkylideneoxindoles and dispiro[oxindole[3, 2′]furan[3′,3′]oxindole]s

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 3850-3858

  Wang, Lei ^a   Zhang, Yan ^a   Hu, Hua You ^a   Fun, Hoong Kun ^b   Xu, Jian Hua ^a  

^a NANJING UNIVERSITY   (China)

^b SCHOOL OF PHYSICS   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC HYDROCARBONS; ATOMS; CARBON; OLEFINS; PHOTODISSOCIATION; REACTION KINETICS;

CYCLOADDITION; HYDROGEN ABSTRACTION; PHOTOREACTIONS; REGIOSELECTIVITY;

PHOTOCHEMICAL REACTIONS;

1 (4 METHOXYPHENYL)PROPYNE; 1 ACETYLISATIN; 1,4 DIPHENYL 1,3 BUTADIYNE; ACETYLENE DERIVATIVE; ACYL RADICAL; ALDEHYDE; ALKYNE; CARBON; CARBONYL DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLACETYLENE; DIPHENYLACETYLENE DERIVATIVE; FUNCTIONAL GROUP; FURAN DERIVATIVE; HYDROGEN; ISATIN DERIVATIVE; OXETENE; OXINDOLE; OXYGEN DERIVATIVE; PHENYL GROUP; PHENYLACETYLENE; RADICAL; SPIRO COMPOUND; SPIROOXETENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CYCLIZATION; CYCLOADDITION; DIASTEREOISOMER; DISSOCIATION; MOLECULAR STABILITY; PHOTOREACTIVITY; RING OPENING; STEREOCHEMISTRY;

ACETYLENE; FURANS; INDOLES; ISATIN; PHOTOCHEMISTRY; STEREOISOMERISM;

EID: 18744381009     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047870+     Document Type: Article

References (109)

1. (a) Friedrich, L. E.; Lam, P. Y.-S. J. Org. Chem. 1981, 46, 306.
2. (b) Friedrich, L. E.; Schuster, G. B. J. Am. Chem. Soc. 1971, 93, 4602.
3. Büchi, G.; Kafron, J. T.; Koller, E.; Rosenthal, D. J. Am. Chem. Soc. 1956, 78, 876.
4. (a) Zimmerman, H. E.; Craft, L. Tetrahedron Lett. 1964, 2131.
5. (b) Bryce-Smith, D.; Fray, G. I.; Gilbert, A. Tetrahedron Lett. 1964, 2137.
6. (c) Bryce-Smith, D.; Gilbert, A.; Johnson, M. G. Tetrahedron Lett. 1968, 2863.
7. (d) Farid, S.; Kothe, W.; Pfundt, G. Tetrahedron Lett. 1968, 4147.
8. (e) Barltrop, J. A.; Hesp, B. J. Chem. Soc. C 1967, 1625.
9. (f) Pappas, S. P.; Portnoy, N. A. J. Org. Chem. 1968, 33, 2200.
10. (g) Bos, H. J. T.; Polman, H.; van Montfort, P. F. E. Chem. Commun. 1973, 188.
11. (h) Serebryakov, E. P.; Kostochka, L. M.; Kucherov, V. F. Zh. Org. Khim. 1973, 9, 2375.
12. (i) Bardamova, M. I.; Berus, E. I.; Vlasov, A. A.; Kotlyarevskii, I. L. Izu. Akad. Nauk SSSR Ser. Khim. 1977, 912.
13. (j) Kim, A. R.; Man, Y. J.; Shim, S. C.; Kim, S. S. J. Photosci. 1997, 4, 49.
14. (k) Bosch, E.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 386.
15. Polman, H.; Mosterd, A.; Bos, H. J. T. Recl. Trav. Chim. 1973, 92, 845 and references therein.
16. (a) Paternò, E.; Chieffi, G. Gazz. Chim. Ital. 1909, 39, 341.
17. (b) Büchi, G.; Inman, C. G.; Lipinsky, E. S. J. Am. Chem. Soc. 1954, 76, 4327.
18. (c) Arnold, D. R. Adv. Photochem. 1968, 6, 301.
19. (d) Jones, G., II In Organic Photochemistry; Padwa, A., Ed; Marcel Dekker: New York, 1981; Vol. 5, p 1.
20. (e) Carless, H. A. J. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984; p 425.
21. (f) Porco, J. A., Jr.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: New York, 1991; Vol. 5, p 151.
22. Kim, S. S.; Kim, A. R.; Cho, I. H.; Shim, S. C. Bull. Korean Chem. Soc. 1989, 10, 57.
23. Turro, N. J.; Dalton, J. C.; Dawes, G.; Farrington, G.; Hautala, R.; Morton, D.; Niemczyk, S.; Schore, N. Acc. Chem. Res. 1972, 5, 92.
24. For reviews, see: (a) Katritzky, A. R.; Boulton, A. J. Advances in Heterocyclic Chemistry; Academic Press: New York, 1975; Vol 18, p 1.
25. (b) Shvekhgeimer, M. G. Khim. Geterotsikl. Soedin. 1996, 291.
26. (a) Haucke, G.; Seidel, B.; Graness, A. J. Photochem. 1987, 37, 139.
27. (b) Kuboyama, A.; Yamazaki, R.; Yabe, S.; Uehara, Y. Bull. Chem. Soc. Jpn. 1969, 42, 10.
28. (c) Galasso, V. Gazz. Chim. Ital. 1976, 106, 571.
29. (a) Xue, J.; Zhang, Y.; Wu, T.; Fun, H.-K.; Xu, J.-H. J. Chem. Soc., Perkin Trans. 1 2001, 183.
30. (b) Zhang, Y.; Xue, J.; Gao, Y.; Fun, H.-K.; Xu, J.-H. J. Chem. Soc., Perkin Trans. 1 2002, 345.
31. Xue, J.; Zhang, Y.; Wang, X.-L.; Fun, H.-K.; Xu, J.-H. Org. Lett. 2000, 2, 2583.
32. (a) Mohammadi, M.; McMahon, G.; Sun, L.; Tang, C.; Hirth, P.; Yeh, B. K.; Hubbard, S. R.; Schlessinger, J. Science 1997, 276, 955.
33. (b) Sun, L.; Tran, N.; Tang, F.; App, H.; Hirth, P.; McMahon, G.; Tang, C. J. Med. Chem. 1998, 41, 2588.
34. (c) Vieth, M.; Commins, D. J. J. Med. Chem. 2000, 43, 3020.
35. (d) Bramson, H. N.; Corona, J.; Davis, S. T.; Dickerson, S. H.; Edelstein, M.; Frye, S. V.; Gampe, R. T., Jr.; Harris, P. A.; Hassell, A.; Holmes, W. D.; Hunter, R. N.; Lackey, K. E.; Lovejoy, B.; Luzzio, M. J.; Montana, V.; Rocque, W. J.; Rusnak, D.; Schewchuk, L.; Veal, J. M.; Walker, D. H.; Kuyper, L. F. J. Med. Chem. 2001, 44, 4339.
36. (e) Sun, L.; Liang, C.; Shirazian, S.; Zhou, Y.; Miller, T.; Cui, J.; Fukuda, J. Y.; Chu, J.-Y.; Nematalla, A.; Wang, X.; Chen, H.; Sistla, A.; Luu, T. C.; Tang, F.; Wei, J.; Tang, C. J. Med. Chem. 2003, 46, 1116.
37. Robinson, R. P.; Reiter, L. A.; Barth, W. E.; Campeta, A. M.; Cooper, K.; Cronin, B. J.; Destito, R.; Donahue, K. M.; Falkner, F. C.; Fiese, E. F.; Johnson, D. L.; Kuperman, A. V.; Liston, T. E.; Malloy, D.; Martin, J. J.; Mitchell, D. Y.; Rusek, F. W.; Shamblin, S. L.; Wright, C. F. J. Med. Chem. 1996, 39, 10.
38. Woodard, C. L.; Li, Z.; Kathcart, A. K.; Terrell, J.; Gerena, L.; Lopez-Sanchez, M.; Kyle, D. E.; Bhattacharjee, A. K.; Nichols, D. A.; Ellis, W.; Prigge, S. T.; Geyer, J. A.; Waters, N. C. J. Med. Chem. 2003, 46, 3877.
39. (a) Cui, C.-B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiol. 1988, 49, 527.
40. (b) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.
41. (c) Attaur-Rahman; Qureshi, M. M.; Muzaffar, A. Heterocycles 1988, 27, 725.
42. For 3-alkylideneoxindoles in the synthesis of spirotryprostantins, see: (a) Wang, H.; Ganesan, A. J. Org. Chem. 2000, 65, 4685.
43. (b) Malinakova, H. C.; Liebeskind, L. S. Org. Lett. 2000, 2, 4083.
44. (c) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666.
45. For 3-alkylideneoxindoles in the synthesis of spirohexaneindole derivatives, see: (a) Chen, Z.; Fan, J.; Rende, A. S. J. Org. Chem. 2004, 69, 79.
46. (b) Okada, K.; Sakuma, H.; Inoue, S. Chem. Lett. 1979, 131.
47. (c) Okada, K.; Mizuno, Y.; Tanino, H.; Kakoi, H.; Inoue, S. Chem. Pharm. Bull. 1992, 40, 1110.
48. (d) Okada, K.; Sakuma, H.; Kondo, M.; Inoue, S. Chem. Lett. 1979, 213.
49. (e) Okada, K.; Kondo, M.; Tanino, H.; Kakoi, H.; Inoue, S. Heterocycles 1992, 34, 589.
50. (f) Richards, C. G.; Thurston, D. E. Tetrahedron 1983, 39, 1817.
51. (g) Richards, C. G.; Ross, M. S. F. Tetrahedron Lett. 1968, 9, 4391.
52. (h) Beccalli, E. M.; Clerici, F.; Gelmi, M. L. Tetrahedron 1999, 55, 8579.
53. (i) Wenkert, E.; Liu, S. Synthesis 1992, 323.
54. For (E)-alkylideneoxindoles as intermediates in the synthesis of the proteasome inhibitors TMC-95A/B, see: (a) Ma, D.; Wu, Q. Tetrahedron Lett. 2000, 41, 9089.
55. (b) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967.
56. (c) Inoue, M.; Furuyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863.
57. (d) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512.
58. (e) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197.
59. (f) Lin, S.; Yang, Z.-Q.; Kwok, B. H. B.; Koldobskiy, M.; Crews, C. M.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6347.
60. For spirocyclic butyrolactone oxindoles natural products, see: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084.
61. (b) Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969.
62. (c) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709.
63. (d) Nakagawa, M.; Sodeoka, M.; Yamaguchi, K.; Hino, T. Chem. Pharm. Bull. 1984, 32, 1373.
64. For synthesis of spirocyclic butyrolactone oxidoles, see: (a) Lawson, W. B.; Patchornik, A.; Witkop, B. J. Am. Chem. Soc. 1860, 82, 5918.
65. (b) Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1984, 29, 1206.
66. (c) Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 2431.
67. (d) Ohki, S.; Nagakasa, T. Chem. Pharm. Bull. 1971, 19, 545.
68. (e) Palla, G.; Marchelli, R.; Casnati, G.; Dossena, A. Gazz. Chim. Ital. 1982, 112, 535.
69. (f) Labroo, R. B.; Labroo, V. M.; King, M. M.; Cohen, L. A. J. Org. Chem. 1991, 56, 3637.
70. (a) Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477.
71. (b) Yanada, R.; Obika, S.; Oyama, M.; Takemoto, Y. Org. Lett. 2004, 6, 2825.
72. (a) Schroeter, S. H.; Orlando, C. M., Jr. J. Org. Chem. 1969, 34, 1181.
73. (b) Turro, N. J.; Wriede, P. A. J. Am. Chem. Soc. 1970, 92, 320.
74. (c) Yang, N. C.; Nussim, M.; Jorgenson, M. J.; Murov, S. Tetrahedron Lett. 1964, 5, 3657.
75. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian 98, Revision A.11.3; Gaussian, Inc.: Pittsburgh, PA, 2002.
76. (a) Galli, C.; Guarnieri, A.; Koch, H.; Mencarelli, P.; Rappoport, Z. J. Org. Chem. 1997, 62, 4072.
77. (b) Galli, C.; Rappoport, Z. Acc. Chem. Res. 2003, 36, 580.
78. (a) Bonazzola, L.; Fenistei, S.; Marx, R. Mol. Phys. 1971, 22, 689.
79. (b) Neilson, G. W.; Symons, M. C. R. J. Chem. Soc., Perkin Trans. 2 1973, 1405.
80. (c) Kasai, P. H.; Whipple, E. B. J. Am. Chem. Soc. 1967, 89, 1033.
81. (d) Bennett, J. E.; Howard, J. A. Chem. Phys. Lett. 1971, 9, 460.
82. (e) Panek, E. J.; Kaiser, L. R.; Whitesides, G. M. J. Am. Chem. Soc. 1977, 99, 3708.
83. (f) Rubin, H.; Fischer, H. Helv. Chim. Acta 1996, 79, 1670.
84. Mcmillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
85. (a) Kraus, G. A.; Kirihara, M. J. Org. Chem. 1992, 57, 3256.
86. (b) Kraus, G. A.; Liu, P. Tetrahedron Lett. 1994, 35, 7723.
87. (c) Pacut, R.; Grimm, M. L.; Kraus, G. A.; Tanko, J. M. Tetrahedron Lett. 2001, 42, 1415.
88. (d) Maruyama, K.; Miyagi, Y. Bull. Chem. Soc. Jpn. 1974, 47, 1303.
89. (e). Bruce, J. M.; Cutts, E. J. Chem. Soc. C 1966, 449.
90. (f) Bruce, J. M.; Creed, D.; Ellis, J. N. J. Chem. Soc. C 1967, 1486.
91. (g) Bruce, J. M.; Dawes, K. J. Chem. Soc. C 1970, 645.
92. (h) Schiel, C.; Oelgemöller, M.; Mattay, J. Synthesis 2001, 1275.
93. (i) Oelgemöller, M.; Schiel, C.; Fröhlich, R.; Mattay, J. Eur. J. Org. Chem. 2002, 2465.
94. (a) Moore, R. F.; Waters, W. A. J. Chem. Soc. 1853, 238.
95. (b) Maruyama, K.; Otsuki, T.; Naruta, Y. Bull. Chem. Soc. Jpn. 1976, 49, 791.
96. (c) Maruyama, K.; Sakurai, H.; Otsuki, T. Bull. Chem. Soc. Jpn. 1977, 50, 2777.
97. (d) Maruyama, K.; Takuwa, A.; Matsukiyo, S.; Soga, O. J. Chem. Soc., Perkin Trans. 1 1980, 1414.
98. (e) Takuwa, A. Bull. Chem. Soc. Jpn. 1977, 50, 2973.
99. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
100. Zhang, Y.; Wang, L.; Zhu, Y.; Xu, J.-H. Eur. J. Org. Chem. 2004, 527.
101. (a) Baldwin, J. E. Chem. Commun. 1976, 734.
102. (b) Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. Chem. Commun. 1976, 736.
103. (c) Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. Chem. Commun. 1980, 482.
104. Ishibashi, H.; Sato, T.; Ikeda, M. Synthesis 2002, 695.
105. Chatgilialoglu, C.; Ferreri, C.; Guerra, M.; Timokhin, V.; Froudakis, G.; Gimisis, T. J. Am. Chem. Soc. 2002, 124, 10765.
106. (a) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564.
107. (b) Ueno, Y.; Moriya, O.; Chino, K.; Watanabe, M.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351.
108. (c) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
109. For a review on Ueno-Stork cyclization, see: Salom-Roig, X. J.; Denes, F.; Renaud, P. Synthesis 2004, 1903.