Photochemistry of o-pyrrolylstilbenes and formation of spiro-2H-pyrroles and their rearrangement to dihydroindoles

Journal of Organic Chemistry

Volumn 71, Issue 25, 2006, Pages 9382-9392

  Basarić, Nikola ^a   Marinić, Željko ^b   Šindler Kulyk, Marija ^c  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b Department of Organic Chemistry ^*  (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERIZATION; NITROGEN COMPOUNDS; SILICA GEL; SUBSTITUTION REACTIONS;

CIS-TRANS-ISOMERIZATION; DIHYDROINDOLES; HYDROGEN TRANSFER; POLYCYCLIC COMPOUNDS; QUINONE DIMETHANE INTERMEDIATES;

PHOTOCHEMICAL REACTIONS;

INDOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; METHANE; POLYCYCLIC HYDROCARBON; PYRROLE DERIVATIVE; QUINONE DERIVATIVE; RADICAL; SILICA GEL; SPIRO COMPOUND; STILBENE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CIS TRANS ISOMERISM; CYCLIZATION; ISOMERIZATION; PHOTOCHEMISTRY; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 33845546715     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061435t     Document Type: Article

References (97)

1. (a) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis: Targets, Strategies, Methods; VCH: Weinheim, 1996.
2. (b) Pelletier, S. V., Ed.; Alkaloids, Chemical and Biological Perspectives: Pergamon: New York, 1999; Vol 14.
3. (c) Pelletier, V., Ed.; Alkaloids, Chemical and Biological Perspectives; Pergamon: New York, 2001; Vol 15.
4. (d) Cordell, G. A., Ed.; The Alkaloids; Academic Press: San Diego, CA, 2002; Vol. 59.
5. (e) Gupton, J. T. Top. Heterocycl. Chem. 2006, 2, 53-92.
6. For example: (a) Terashima, M.; Koyama, K.; Konaoka, Y. Chem. Pharm. Bull. 1978, 26, 630-632.
7. (b) Itahara, T. Synthesis 1979, 151-152.
8. (c) New, J. S.; Yevich, J. P. J. Heterocycl. Chem. 1984, 21, 1355-1360.
9. (d) Stetter, H.; Haese, W. Chem. Ber. 1984, 117, 682-693.
10. (e) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317-3320.
11. (f) Padwa, A.; Dean, D. C.; Hertzog, D. L.; Nadler, W. R.; Zhi, L. Tetrahedron 1992, 48, 7565-7580.
12. (g) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64.
13. (h) Antonio, Y.; De La Cruz, Ma. E.; Galeazzi, E.; Guzman, A.; Bray, B. L.; Greenhouse, R.; Kurz, L. J.; Lustig, D. A.; Maddox, M. L.; Muchowski, J. M. Can. J. Chem. 1994, 72, 15-22.
14. (i) Nudelman, A.; Marcovici, D.; Nachum, A. Heterocycles 1994, 38, 751-758.
15. (j) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc. Perkin Trans. 1 1996, 675-682.
16. (k) McNab, H.; Parsons, S.; Stevenson, E. J. Chem. Soc. Perkin Trans. 1 1999, 2047-2049.
17. For example: (a) Atanes, N.; Guitán, E.; Saá, C.; Castedo, L.; Saá, J. M. Tetrahedron Lett. 1987, 28, 817-820.
18. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1990, 46, 4003-4018.
19. (c) Polossek, T.; Ambros, R.; Von Angerer, S.; Brandl, G.; Mannschreck, A.; von Angerer, E. J. Med. Chem. 1992, 35, 3537-3547.
20. (d) Grigg, R.; Kennwell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423-10430.
21. (e) Atanes, N.; Pérez, S.; Guitán, E.; Castedo, L.; Saá, J. M. Tetrahedron 1994, 38, 11257-11266.
22. (f) Elwan, N. M.; Abdelhadi, H. A.; Abdellah, T. A.; Hassaneen, H. M. Tetrahedron 1996, 52, 3451-3456.
23. (g) Nemes, P.; Katjár-Peredy, M.; Scheiber, P. Synlett. 1996, 623-624.
24. (h) Banwell, M.; Flynn, B.; Hockless, D. Chem. Commun. 1997, 2259-2260.
25. (i) Zhao, B.-X.; Eguchi, S. J. Chem. Soc. Perkin. Trans. 1 1997, 2973-2977.
26. (j) Fujii, H.; Iwafuji, K.; Sawae, Y.; Abe, N.; Kakehi, A. Heterocycles 2003, 59, 63-66.
27. (k) De, Koning, C. B.; Michael, J. P.; Pathak, R.; van Otterlo, W. A. L. Tetrahedron Lett. 2004, 45, 1117-1119.
28. (l) Ploypradith, P.; Kagan, R. K.; Ruchirawat, S. J. Org. Chem. 2005, 70, 5119-5125.
29. (m) Pla, D.; Marchal, A.; Olsen, C. A.; Albericio, F.; Álvarez, M. J. Org. Chem. 2005, 70, 8231-8234.
30. For example: (a) Katritzky, A. R.; Wang, Z.; Savage, G. P. J. Heterocycl. Chem. 1991, 28, 321-323.
31. (b) Brown, F. C. R.; Coulston, K. J.; Eastwood, F. W.; Moffat, M. R. Tetrahedron 1992, 36, 7763-7774.
32. (c) Suginome, H.; Sakurai, H.; Sasaki, A.; Tekeuchi, H.; Kobayashi, K. Tetrahedron 1994, 50, 8293-8300.
33. (d) Pinna, G. A.; Prisi, M. A.; Paglietti, G. Farmaco 1994, 49, 121-126.
34. (e) Macchia, M.; Manera, C.; Nencetti, S.; Rossello, A.; Broccali, G.; Limonta, D. Farmaco 1996, 51, 75-78.
35. (f) Gonzalez, E.; Pindur, U.; Schollmeyer, D. J. Chem. Soc. Perkin Trans. 1 1996, 1767-1771.
36. (g) Kobayashi, K.; Taki, T.; Kawakita, M.; Uchida, M.; Morikawa, O.; Konishi, H. Heterocycles 1999, 51, 349-354.;
37. (h) Barolo, S. M.; Lukach, A. E.; Rossi, R. A. J. Org. Chem. 2003, 68, 2807-2811.
38. (a) Šindler-Kulyk, M.; Špoljarić, L.; Marinić, Ž. Heterocycles 1989, 29, 679-682.
39. (b) Šindler-Kulyk, M.; Metelko, B.; Stiplošek, Z. Croat. Chem. Acta 1989, 62, 81-87.
40. (c) Šindler-Kulyk, M.; Stiplošek, Z.; Vojnović, D.; Metelko, B.; Marinić, Ž. Heterocycles 1991, 32, 2357-2363.
41. (d) Sindler-Kulyk, M.; Kragol, G.; Piantanida, I.; Tomšić, S.; Vujković, Cvijin, I.; Marinić, Z.; Metelko, B. Croat. Chem. Acta 1996, 69, 1593-1602.
42. (e) Vujković Cvijin, I.; Marinić, Ž.; Šindler-Kulyk, M. Spectrosc. Lett. 1998, 31, 989-1000.
43. (f) Šindler-Kulyk, M.; Škorić, I.; Tomšić, S.; Marinić, Ž.; Mrvoš-Sermek, D. Heterocycles 1999, 51, 1355-1369.
44. (g) Škorić, I.; Marinić, Ž.; Šindler-Kulyk, M. Heterocycles 2000, 53, 55-68.
45. (h) Škorić, I.; Basarić, N.; Marinić, Ž.; Šindler-Kulyk, M. Heterocycles 2001, 55, 1889-1896.
46. (i) Škorić, I.; Hutinec, A.; Marinić, Ž.; Šindler-Kulyk, M. ARKIVOC 2003, 14, 87-97.
47. (j) Škorić, I.; Marinić, Ž.; Šindler-Kulyk, M. Croat. Chem. Acta 2004, 77, 161-166.
48. (k) Škorić, I.; Basarić, N.; Marinić, Ž.; Šindler-Kulyk, M.; Višnjevac, A.; Kojić- Prodić, B. Chem. Eur. J. 2005, 11, 543-551.
49. (a) Šindler-Kulyk, M.; Tomšić, S.; Marinić, Ž.; Metelko, B. Recl. Trav. Chim. Pays-Bas 1995, 114, 476-479.
50. (b) Basarić, N.; Tomšić, S.; Marinić, Ž.; Šindler-Kulyk, M. Tetrahedron 2000, 56, 1587-1593.
51. (c) Basarić, N.; Marinić, Ž.; Šindler-Kulyk, M. Tetrahedron Lett. 2001, 42, 3641-3643.
52. (d) Višnjevac, A.; Basarić, N.; Kojić-Prodić, B.; Šindler-Kulyk, M. Acta Crystallogr. E 2001, 57, 01252-01254.
53. (e) Rademacher, P.; Basarić, N.; Kowski, K.; Šindler-Kulyk, M. Eur. J. Org. Chem. 2002, 551-556.
54. (f) Basarić, N.; Višnjevac, A.; Kojić-Prodić, B.; Griesbeck, A.; Šindler-Kulyk, M. Photochem. Photobiol. Sci. 2002, 1, 1017-1023.
55. (g) Basarić, N.; Iveković, D.; Zimmermann, B.; Marinić, Ž.; Kowski, K.; Rademacher, P.; Šindler-Kulyk, M. J. Photochem. Photobiol. A 2003, 154, 123-130.
56. (h) Basarić, N.; Marinić, Ž.; Šindler-Kulyk, M. J. Org. Chem. 2003, 68, 7524-7527.
57. Basarić, N.; Marinić, Ž.; Šindler-Kulyk, M. Tetrahedron Lett. 2003, 44, 7337-7340.
58. (a) Kubota, T.; Sakurai, H. Chem. Lett. 1972, 923-926.
59. (b) Kubota, T.; Sakurai, H. Chem. Lett. 1972, 1249-1250.
60. (c) Koshima, H.; Ichimura, H.; Hirotsu, K.; Miyahara, I.; Wang, Y.; Matsuura, T. J. Photochem. Photobiol. A. Chem. 1995, 85, 225-229.
61. (d) Austin, M.; Covell, C.; Gilbert, A.; Hendrickx, R. Liebigs Ann./Recueil 1997, 943-946.
62. (a) Lewis, F. D.; Crompton, E. M. SET Addition of Amines to Alkenes. In CRC Handbook of Photochemistry and Photobiology; Horspool, W., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004.
63. (b) Lewis, F. D. Adv. Electron Transfer Chem. 1996, 5, 1-39.
64. Groenendaal, L.; Peerlings, H. W. I.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Synth. Met. 1995, 69, 467-470.
65. (a) Bonini, F.; Tiecco, M. Gazz. Chim. Ital. 1966, 96, 1792-1805.
66. (b) de Meijere, A.; Song, Z. Z.; Lansky, A.; Hyuda, S.; Rauch, K.; Noltemeyer, M.; König, B.; Knieriem, B. Eur. J. Org. Chem. 1998, 2289-2299.
67. (a) James, J. N. G.; Williams, G. J. B. Can. J. Chem. 1972, 50, 2407-2412.
68. (b) Laurent, A.; Mison, P.; Nafti, A.; Pellissier, N. Tetrahedron Lett. 1978, 46, 4511-4514.
69. (c) Jones, K.; Ho, T. C. T.; Wilkinson, J. Tetrahedron Lett. 1995, 37, 6743-6744.
70. (d) Escolano, C.; Jones, K. Tetrahedron Lett. 2000, 41, 8951-8955.
71. (e) Escolano, C.; Jones, K. Tetrahedron 2002, 58, 1453-1464.
72. (f) Spivey, A. C.; Frampton, C. S.; Battersby, A. R. J. Chem. Soc. Perkin Trans. 1 1996, 2103-2110.
73. (g) Hawker, C. J.; Stark, W. M.; Spivey, A. C.; Raithby, P. R.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc. Perkin Trans. 1 1998, 1493-1508.
74. (h) Hawker, C. J.; Spivey, A. C.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc. Perkin Trans. 1 1998, 1509-1517.
75. Jossang, A.; Jossang, P.; Hadi, H. A.; Sévenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527-6530.
76. Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 39, 12651-1266.
77. Mathewson, J. H.; Corwin, A. H. J. Am. Chem. Soc. 1961, 83, 135-137.
78. (a) Lewis, F. D.; Kalgutkar, R. S.; Yang, J.-S. J. Am. Chem. Soc. 1999, 121, 12045-12053.
79. (b) Lewis, F. D.; Kalgutkar, R. S. J. Phys. Chem. A 2001, 105, 285-291.
80. Olmsted, J., III. J. Phys. Chem. 1979, 83, 2581-2584.
81. Bohne, C.; Ihmels, H.; Weidelich, M.; Yihwa, C. J. Am. Chem. Soc. 2005, 127, 17158-17159.
82. Roberts, J. C.; Pincock, J. A. J. Org. Chem. 2006, 71, 1480-1492.
83. (a) Saltiel, J.; Charlton, J. L. Rearrangements in ground and excited states; de Mayo, P., Ed.; Academic Press; New York, 1980.
84. (b) Dutt, G. B.; Konitsky, W.; Waldeck, D. H. Chem. Phys. Lett. 1995, 245, 437-440.
85. (c) Penn, J. H.; Gan, L.-X.; Eaton, T. A.; Chan, E. Y.; Lin, Z. J. Org. Chem. 1988, 53, 1519-1523.
86. (d) Lewis, F. D.; Hoyle, C. E. J. Am. Chem. Soc. 1977, 11, 3779-3786.
87. (a) Mazzucato, U. Pure Appl. Chem. 1982, 54, 1705-1721.
88. (b) Saltiel, J.; Sun, Y.-P. Photocromism Molecules and Systems; Durr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990.
89. (a) Hara, M.; Samori, S.; Xichen, C.; Fujitsuka, M.; Majima, T. J. Org. Chem. 2005, 70, 4270-4374.
90. (b) Miranda, M. A.; Angeles, Izquierdo, M.; Galindo, F. J. Org. Chem. 2002, 67, 4138-4142.
91. (c) Majima, T.; Tojo, S.; Ishida, A.; Takamuku, S. J. Org. Chem. 1996, 61, 7793-7800.
92. (d) Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401, 449.
93. Samori, S.; Hara, H.; Tojo, S.; Fujitsuka, M.; Majima, T. J. Photochem. Photobiol. A: Chem. 2006, 179, 115-124.
94. (a) Konosonokos, A.; Wright, P. J.; Tsao, M.-L.; Pika, J.; Novak, K.; Mandel, S. M.; Krause, Bauer, J. A.; Bohne, C.; Gudmundsdóttir, A. D. J. Org. Chem. 2005, 70, 2763-2770.
95. (b) Johnston, L. J.; Scaiano, J. C. Chem. Rev. 1989, 89, 521-547.
96. Miranda, M. A.; Font-Sanchis, E.; Pérez-Prieto, J.; Scaiano, J. C. J. Org. Chem. 2001, 66, 2717-2721.
97. (b) Font-Sanchis, E.; Miranda, M. A.; Pérez-Prieto, J.; Scaiano, J. C. J. Org. Chem. 2002, 67, 6131-6135.