Diels-Alder reactions of 4-alkenylthiazoles: A new approach to thiazole functionalization

Journal of Organic Chemistry

Volumn 72, Issue 6, 2007, Pages 2097-2105

  Alajarín, Mateo ^a   Cabrera, José ^a   Pastor, Aurelia ^a   Sánchez Andrada, Pilar ^a   Bautista, Delia ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDUCT; FUNCTIONALIZATION; HIGHEST OCCUPIED MOLECULAR ORBITAL (HOMO) ENERGIES; MICHAEL ADDITION;

CHEMICAL BONDS; CYCLOADDITION; DEHYDROGENATION; REACTION KINETICS; SUBSTITUTION REACTIONS;

NITROGEN COMPOUNDS;

4 ALKENYLTHIAZOLE DERIVATIVE; MALEIC ANHYDRIDE; MALEIMIDE DERIVATIVE; NAPHTHOQUINONE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL BINDING; DANISHEFSKY KITAHARA REACTION; DEHYDROGENATION; DIELS ALDER REACTION; HIGHEST OCCUPIED MOLECULAR ORBITAL ENERGY; HYDROGEN BOND; MICHAEL ADDITION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALKADIENES; MALEIC ANHYDRIDES; MALEIMIDES; MODELS, MOLECULAR; NAPHTHOQUINONES; THIAZOLES;

EID: 33947237931     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062417e     Document Type: Article

References (80)

1. Dewick, P. M. In Medicinal Natural Products. A Biosynthetic Approach, 2nd ed.; Wiley: Chichester, U.K., 2002.
2. (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 315-399.
3. (b) Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction-Selected Practical Methods; Wiley: Chichester, U.K., 2002.
4. (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
5. Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
6. (a) Sepúlveda-Arques, J.; Abarca-González, B.; Medio-Simón, M. Adv. Heterocycl. Chem. 1995, 63, 339-401.
7. (b) Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction-Selected Practical Methods; Wiley: Chichester, U.K., 2002; pp 56-64.
8. Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction-Selected Practical Methods; Wiley: Chichester, U.K., 2002; pp 40-41.
9. (a) Jones, G.; Rafferty, P. Tetrahedron Lett. 1978, 19, 2731-2734.
10. (b) Jones, G.; Rafferty, P. Tetrahedron 1979, 35, 2027-2033.
11. (a) Jones, R. A.; Marriott, M. T. P.; Rosenthal, W. P.; Sepúlveda-Arques, J. J. Org. Chem. 1980, 45, 4515-4519.
12. (b) Xiao, D.; Ketcha, D. M. J. Heterocycl. Chem. 1995, 32, 499-503.
13. (c) Noland, W. E.; Wann, S. R. J. Org. Chem. 1979, 44, 4402-4410.
14. (d) Eitel, M.; Pindur, U. J. Org. Chem. 1990, 55, 5368-5374.
15. (e) Pindur, U.; Kim, M.-H.; Rogge, M.; Massa, W.; Molinier, M. J. Org. Chem. 1992, 57, 910-915.
16. (f) Back, T. G.; Pandyra, A.; Wulff, J. E. J. Org. Chem. 2003, 68, 3299-3302.
17. (g) Du, H.; He, Y.; Sivappa, R.; Lovely, C. J. Synlett 2006, 7, 965-992.
18. (h) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535-1538.
19. (i) Dransfield, P. J.; Wang, S.; Dilley, A.; Romo, D. Org. Lett. 2005, 7, 1679-1682.
20. (j) Marrocchi, A.; Minuti, L.; Taticchi, A.; Scheeren, H. W. Tetrahedron 2001, 57, 4959-4965.
21. (k) Le Strat, F.; Vallete, H.; Toupet, L.; Maddaluno, J. Eur. J. Org. Chem. 2005, 5296-5305.
22. (l) Scully, J. F.; Brown, E. V. J. Am. Chem. Soc. 1953, 75, 6329-6330.
23. (m) Moody, C. J.; Rees, C. W.; Tsoi, S. C. J. Chem. Soc., Perkin Trans. I 1984, 915-920.
24. Corral, C.; Lissavetzky, J.; Manzanares, I. Synthesis 1997, 29-31.
25. Thiazole and its Derivatives; Metzger, J. V., Ed.; Wiley: New York, 1979.
26. (a) Hantzsch, A. R.; Weber, J. H. Ber. Dtsch. Chem. Ges. 1887, 20, 3118-3132.
27. (b) Schwarz, G. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. 3, pp 332-333.
28. Hudson, R. F.; Chopard, P. A. J. Org. Chem. 1963, 28, 2446-2447.
29. For reviews see (a) Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753-786.
30. (b) Jorgensen, K. A. Eur. J. Org. Chem. 2004, 2093-2102.
31. (a) Fukui, K. Tetrahedron Lett. 1965, 6, 2009-2015.
32. (b) Fukui, K. Acc. Chem. Res. 1971, 4, 57-64.
33. (c) Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17-22.
34. (d) Woodward, R. B.; Hoffmann, R. In The Conservation of the Orbital Theory; Verlag Chemie: Weinheim, Germany, 1970.
35. (e) Fleming, I. In Frontier Orbitals and Organic Chemical Reactivity; Wiley: New York, 1976.
36. (f) Houk, K. N. In Pericyclic Reactions; Lehr, R. E., Marchand, A. P., Eds.; Academic Press: London, 1977; Vol. 2, p 181.
37. (g) Houk, K. N. Acc. Chem. Res. 1975, 8, 361-369.
38. (a) Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807-7808.
39. (b) Danishefsky, S. Acc. Chem. Res. 1981, 14, 400-406.
40. (c) Banville, J.; Brassard, P. J. Chem. Soc., Perkin. Trans. I 1976, 1852-1856.
41. (d) Danishefsky, S.; Singh, R. K.; Gammill, R. B. J. Org. Chem. 1978, 43, 379-380.
42. (e) Ibuka, T.; Mori, Y.; Inubushi, Y. Tetrahedron Lett. 1976, 17, 3169-3172.
43. For 1,3-bis(dimethylamino) dienes, see (a) Gompper, R.; Sobotta, R. Tetrahedron Lett. 1979, 20, 921-924.
44. (b) Gompper, R.; Heinemann, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 216-217.
45. For 1-amino-3-siloxy dienes, see (a) Smith, A. B., III; Wexler, B. A.; Tu, C.-Y.; Konopelski, J. P. J. Am. Chem. Soc. 1985, 107, 1308-1320.
46. (b) Comins, D. L.; Al-awar, R. S. J. Org. Chem. 1992, 57, 4098-4103.
47. (c) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246-3247.
48. (d) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252-5253.
49. (e) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039-3052.
50. (f) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166.
51. (g) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1999, 121, 9562-9573.
52. (h) Kozmin, S. A.; Green, M. T.; Rawal, V. H. J. Org. Chem. 1999, 64, 8045-8047.
53. (a) Sustmann, R.; Schubert, R. Tetrahedron Lett. 1972, 13, 2739-2742.
54. (b) Sustmann, R.; Schubert, R. Angew. Chem., Int. Ed. Engl. 1972, 11, 840.
55. (c) Overman, L. E.; Taylor, G. F.; Houk, K. N.; Dometsmith, L. N. J. Am. Chem. Soc. 1978, 100, 3182-3189.
56. (d) Kawasaki, I.; Sakaguchi, N.; Khadeer, A.; Yamashita, M.; Ohta, S. Tetrahedron 2006, 62, 10182-10192.
57. (e) Sheng, Y.; Leszczynski, J. Tetrahedron 2006, 62, 7014-7020.
58. (f) Landreau, C.; Janvier, P.; Julienne, K.; Meslin, J. C.; Deniaud, D. Tetrahedron 2006, 62, 9226-9231.
59. (g) See also ref 16h.
60. 4-Alkenylthiazoles 1f-i have not been described previously in the literature. For the preparation of thiazole 1j, see Schilling, C. L., Jr.; Mulvaney, J. E. Macromolecules 1968, 1, 445-451.
61. (a) Houk, K. N.; Strozier, R. W. J. Am. Chem. Soc. 1973, 95, 4094-4096.
62. (b) Carruthers, W. In Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, U.K., 1990; pp 50-53.
63. (c) Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction-Selected Practical Methods; Wiley: Chichester, U.K., 2002; pp 99-142.
64. (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
65. (b) Fernández Sainz, Y.; Raw, S. A.; Taylor, R. J. K. J. Org. Chem. 2005, 70, 10086-10095.
66. (c) Pinto, D. C. G. A.; Silva, A. M. S.; Brito, C. M.; Sandulache, A.; Carrillo, J. R.; Prieto, P.; Díaz-Ortiz, A.; de la Hoz, A.; Cavaleiro, J. A. S. Eur. J. Org. Chem. 2005, 2973-2986.
67. (d) Silva, V. L. M.; Silva, A. M. S.; Pinto, D. C. G. A.; Cavaleiro, J. A. S. Synlett 2006, 1369-1373.
68. (a) Lovely, C. J.; Du, H.; Rasika Dias, H. V. Org. Lett. 2001, 3, 1319-1322.
69. (b) Lovely, C. J.; Du, H.; He, Y.; Rasika Dias, H. V. Org. Lett. 2004, 6, 735-738.
70. Jackman, L. M.; Sternhell, S. In Applications of Nuclear Magnetic Resonance Spectroscope in Organic Synthesis; Pergamon Press: Oxford, U.K., 1969; pp 334-341.
71. (a) Tietze, L. F.; Bratz, M.; Machinek, R.; v. Kiedrowski, G. J. Org. Chem. 1987, 52, 1638-1640.
72. (b) Shimizu, T.; Murakami, H.; Kamigata, N. J. Org. Chem. 1999, 64, 8489-8494.
73. Partial or full dehydrogenation of cycloadducts resulting from the reaction of dienes with quinones is well documented; see (a) Tominaga, Y.; Lee, M. L.; Castle, R. N. J. Heterocycl. Chem. 1981, 18, 967-972.
74. (b) Noland, W. E.; Konkel, M. J.; Tempesta, M. S.; Cink, R. D.; Powers, D. M.; Schlemper, E. O.; Barnes, C. L. J. Heterocycl. Chem. 1993, 30, 183-192.
75. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; 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.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03; Gaussian, Inc.; Pittsburgh, PA, 2003.
76. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. In Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 71-82 and references cited therein.
77. (a) Parr, R. G.; Yang, W. In Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
78. (b) Bartolotti, L. J.; Fluchichk, K. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyds, D. B., Eds.; VCH Publishers: New York, 1996; Vol. 7, pp 187-216.
79. (c) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980.
80. (d) Ziegler, T. Chem. Rev. 1991, 91, 651-667.