Polar hetero-Diels-Alder reactions of 4-alkenylthiazoles with 1,2,4-triazoline-3,5-diones: An experimental and computational study

Journal of Organic Chemistry

Volumn 73, Issue 3, 2008, Pages 963-973

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

^a Campus de Espinardo   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL METHODS; ENERGY BARRIERS; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

DIASTEREOMERIC TRANSITION STATES; HETEROPOLYCYCLIC SYSTEMS; STEREOCONTROL;

ALCOHOLS;

4 ALKENYLTHIAZOLE DERIVATIVE; 4 PHENYL 1,2,4 TRIAZOLINE 3,5 DIONE DERIVATIVE; 4 STYRYLTHIAZOLE DERIVATIVE; ALKENE DERIVATIVE; METHYL GROUP; PHENYL GROUP; POLYCYCLIC HYDROCARBON; REAGENT; THIAZOLE DERIVATIVE; TRIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOMERISM; DIELS ALDER REACTION; EXPERIMENTAL STUDY; HETEROPOLYCYCLIC SYSTEM; MATHEMATICAL COMPUTING; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION;

EID: 84962343716     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7021668     Document Type: Article

References (121)

1. (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 315-399.
2. (b) Fringuelli, F.; Taticchi, A. In The Diels - Alder Reaction - Selected Practical Methods; Wiley: Chichester, UK, 2002.
3. (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
4. (a) Sepúlveda-Arques, J.; Abarca-González, B.; Medio-Simón, M. Adv. Heterocycl. Chem. 1995, 63, 339-401.
5. (b) Çavdar, H.; Saraçoǧlu, N. J. Org. Chem. 2006, 71, 7793-7799.
6. (a) Jones, R. A.; Marriott, M. T. P.; Rosenthal, W. P.; Sepúlveda-Arques, J. J. Org. Chem. 1980, 45, 4515-4519.
7. (b) Xiao, D.; Ketcha, D. M. J. Heterocycl. Chem. 1995, 32, 499-503.
8. (c) Noland, W. E.; Wann, S. R. J. Org. Chem. 1979, 44, 4402-4410.
9. (d) Eitel, M.; Pindur, U. J. Org. Chem. 1990, 55, 5368-5374.
10. (e) Pindur, U.; Kim, M.-H.; Rogge, M.; Massa, W.; Molinier, M. J. Org. Chem. 1992, 57, 910-915.
11. (f) Back, T. G.; Pandyra, A.; Wulff, J. E. J. Org. Chem. 2003, 68, 3299-3302.
12. (g) Du, H.; He, Y.; Sivappa, R.; Lovely, C. J. Synlett 2006, 7, 965-992.
13. (h) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535-1538.
14. (i) Dransfield, P. J.; Wang, S.; Dilley, A.; Romo, D. Org. Lett. 2005, 7, 1679-1682.
15. (j) Marrocchi, A.; Minuti, L.; Taticchi, A.; Scheeren, H. W. Tetrahedron 2001, 57, 4959-4965.
16. (k) Le Strat, F.; Vallete, H.; Toupet, L.; Maddaluno, J. Eur. J. Org. Chem. 2005, 5296-5305.
17. (l) Scully, J. F.; Brown, E. V. J. Am. Chem. Soc. 1953, 75, 6329-6330.
18. (m) Moody, C. J.; Rees, C. W.; Tsoi, S. C. J. Chem. Soc., Perkin Trans. 1 1984, 915-920.
19. Alajarín, M.; Cabrera, J.; Pastor, A.; Sánchez-Andrada, P.; Bautista, D. J. Org. Chem. 2007, 72, 2097-2105.
20. Manoharan, M.; De Proft, F.; Geerlings, P. J. Chem. Soc., Perkin Trans. 2 2000, 1767-1773.
21. (a) Moody, C. J. Adv. Heterocycl. Chem. 1982, 30, 1-45.
22. (b) Rádl, S. Adv. Heterocycl. Chem. 1997, 67, 119-205.
23. Anastassiou, A. G.; Yakali, E. J. Chem. Soc., Chem. Commun. 1972, 92-93.
24. (a) Askani, R.; Chesick, J. P. Chem. Ber. 1973, 106, 8-19.
25. (b) Imagawa, T.; Sueda, N.; Kawanisi, M. J. Chem. Soc., Chem. Commun. 1972, 388.
26. (c) Kobal, V. M.; Gibson, D. T.; Davies, R. E.; Garza, A. J. Am. Chem. Soc. 1973, 95, 4420-4421.
27. (a) Poutsma, M. L.; Ibarbia, P. A. Tetrahedron Lett. 1970, 11, 4967-4970.
28. (b) Poutsma, M. L.; Ibarbia, P. A. J. Am. Chem. Soc. 1971, 93, 440-450.
29. (a) Ochi, K.; Matsunaga, I.; Nagano, H.; Fukushima, M.; Shindo, M.; Kaneko, C.; Ishikawa, M.; DeLuca, H. F. J. Chem. Soc., Perkin Trans. 1 1979, 165-169.
30. (b) Bosworth, N.; Emke, A.; Midgley, J. M.; Moore, C. J.; Whalley, W. B.; Ferguson, G.; Marsh, W. C. J. Chem. Soc., Perkin Trans. 1 1977, 805-809.
31. (c) Barton, D. H. R.; Gunatilaka, A. A. L.; Nakanishi, T.; Patin, H.; Widdowson, D. A.; Worth, B. R. J. Chem. Soc., Perkin Trans. 1 1976, 821-826.
32. Vougioukalakis, G. C.; Orfanopoulos, M. Synlett 2005, 713-731.
33. (a) Jensen, F.; Foote, C. S. J. Am. Chem. Soc. 1987, 109, 6376-6385.
34. (b) Clenan, E. L.; Earlywine, A. D. J. Am. Chem. Soc. 1987, 109, 7104-7110.
35. (a) Chen, J. S.; Houk, K. N.; Foote, C. S. J. Am. Chem. Soc. 1998, 120, 12303-12309.
36. (b) Singleton, D. A.; Schulmeier, B. E.; Hang, C.; Thomas, A. A.; Leung, S.-W.; Merrigan, S. R. Tetrahedron 2001, 57, 5149-5160.
37. (c) Leach, A. G.; Houk, K. N. Chem. Commun. 2002, 1243-1255.
38. (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876-889.
39. (b) Maddaluno, J. Synlett 2006, 41, 2534-2547.
40. (a) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1999, 121, 9562-9573.
41. (b) Janey, J. M.; Iwama, T.; Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 2000, 65, 9059-9068.
42. (c) Garner, P.; Anderson, J. T.; Turske, R. A. Chem. Commun. 2000, 1579-1580.
43. (d) Søndergaard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324-2331.
44. (e) Urabe, H.; Kusaka, K.; Suzuki, D.; Sato, F. Tetrahedron Lett. 2002, 43, 285-289.
45. (f) Kuethe, J. T.; Brooks, C. A.; Comins, D. L. Org. Lett. 2003, 5, 321-323.
46. The synthesis of 4-alkenylthiazoles 1a-d has been reported previously by the authors, see ref. 4.
47. These compounds were obtained from the reaction of dienes 1 with N-substituted maleimides in acetonitrile at 120°C, see ref 4.
48. Roa, R.; O'Shea, K. E. Tetrahedron 2006, 62, 10700-10708.
49. Vassilikogiannakis, G.; Elemes, Y.; Orfanopoulos, M. J. Am. Chem. Soc. 2000, 122, 9540-9541.
50. (a) Hantzsch, A. R.; Weber, J. H. Ber. Dtsch. Chem. Ges. 1887, 20, 3118-3132.
51. (b) Schwarz, G. Organic Syntheses; Wiley: New York, 1955; Collect. III, pp 332 and 333.
52. (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257-3262.
53. (b) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633.
54. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897-3900.
55. (d) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478.
56. (e) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190-9193.
57. (f) Crisp, G. T.; Gebauer, M. G. J. Org. Chem. 1996, 61, 8425-8431.
58. (g) Ruijter, E.; Schültingkemper, H.; Wessjohann, L. A. J. Org. Chem. 2005, 70, 2820-2823.
59. Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206-4212.
60. (a) Caramella, P.; Rondan, N. G.; Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2438-2440.
61. (b) Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
62. (c) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-1117.
63. (a) Johnson, F. Chem. Rev. 1968, 68, 375-413.
64. (b) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
65. Turner, C. I.; Paddon-Row, M. N.; Willis, A. C.; Sherburn, M. S. J. Org. Chem. 2005, 70, 1154-1163.
66. (a) McCarrick, M. A.; Wu, Y.-D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1499-1500.
67. (b) McCarrick, M. A.; Wu, Y.-D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330-3343.
68. Although steric effects depend so much upon the precise direction from which a reagent approaches that there can be no single scale for evaluating the effective size of a group, we assume that H < Me < Ph, see: Fleming, I.; Lewis, J. J. J. Chem. Soc., Chem. Commun. 1985, 149-151.
69. These steric requirements are based on A values, see: McGarvey, G. J.; Williams, J. M. J. Am. Chem. Soc. 1985, 107, 1435-1437.
70. (a) 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.
71. (b) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980.
72. (c) Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512-7516.
73. (d) Ziegler, T. Chem. Rev. 1991, 91, 651-667.
74. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; 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.
75. See for example: (a) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043.
76. (b) Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8378-8388.
77. (c) Garcia, J. I.; Martinez-Merino, V.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1998, 120, 2415-2420.
78. (d) Domingo, L. R.; Arnó, M.; Andrés, J. J. Am. Chem. Soc. 1998, 120, 1617-1618.
79. (e) Liu, J.; Niwayama, S.; You, Y.; Houk, K. N. J. Org. Chem. 1998, 63, 1064-1073.
80. (f) Birney, D. M. J. Am. Chem. Soc. 2000, 122, 10917-10925.
81. (a) Fukui, K. J. Phys. Chem. 1970, 74, 4161-4162.
82. (b) Fukui, K. Acc. Chem. Res. 1981, 14, 363-368.
83. (a) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
84. (b) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1991, 95, 5853-5860.
85. Wiberg, K. B. Tetrahedron 1968, 24, 1083-1096.
86. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
87. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
88. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434-1445.
89. (a) Borden, W. T.; Loncharich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213-236.
90. (b) Moyano, A.; Pericas, M. A.; Valenti, E. J. Org. Chem. 1989, 54, 573-582.
91. (c) These indexes also have been used to characterize cycloaddition reactions other than [4+2], see for example: Lecea, B.; Ayerbe, M.; Arrieta, A.; Cossío, F. P.; Branchadell, V.; Ortuño, R. M.; Baceiredo, A. J. Org. Chem. 2007, 72, 357-366.
92. (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
93. (b) Simkin, B. Y.; Sheikhet, I. Quantum Chemical and Statical Theory of Solutions - A Computational Approach; Ellis Horwood: London, UK, 1995; pp 78-101.
94. (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129.
95. (b) Cammi, R.; Tomasi, J. J. Chem. Phys. 1994, 100, 7495-7502.
96. (c) Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
97. Whereas in exo-TS3a the more advanced forming bond is C5-N, in exo-TS3b it is the C1-N bond. We have located another exo transition state for the reaction of HTAD with 13b where the more advanced forming bond is C5-N, but it is higher in energy than exo-TS3b, see the Supporting Information. In contrast, for the reaction of HTAD with 13a we have only found one exo transition state, exo-TS3a.
98. A similar difference in the degree of twisting has been reported by Houk for the endo and exo transition states computed for the Diels-Alder reaction of HTAD with butadiene, see ref 13a.
99. (a) Varandas, A. J. C.; Formosinho, S. J. F. J. Chem. Soc., Faraday Trans. 2 1986, 82, 953-962.
100. (b) Lendvay, G. THEOCHEM 1988, 167, 331-338.
101. (c) Lendvay, G. J. Phys. Chem. 1989, 93, 4422-4429.
102. (d) Lendvay, G. J. Phys. Chem. 1994, 98, 6098-6104.
103. See for example: (a) Domingo, L. R.; Arnó, M.; Andrés, J. J. Org. Chem. 1999, 64, 5867-5875.
104. (b) Gómez-Bengoa, E.; Helm, M.; Plant, A.; Harrity, J. P. A. J. Am. Chem. Soc. 2007, 129, 2691-2699.
105. (c) Domingo, L. R. Tetrahedron 2002, 58, 3765-3774.
106. Domingo, L. R.; Aurell, M. J.; Pérez, P.; Contreras, R. J. Org. Chem. 2003, 68, 3884-3890.
107. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University: New York, 1989.
108. Pearson, R. G. Chemical Hardness, Applications from Molecules to Solids; Wiley-VCH Verlag GMBH: Weinheim, Germany, 1997.
109. Parr, R. G.; von Szentpaly, L.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922-1924.
110. (a) Domingo, L. R.; Arnó, M.; Contreras, R.; Pérez, P. J. Phys. Chem. A 2002, 106, 952-961.
111. (b) Domingo, L. R.; Aurell, M. J. J. Org. Chem. 2002, 67, 959-965.
112. (c) Domingo, L. R.; Asensio, A.; Arroyo, P. J. Phys. Org. Chem. 2002, 15, 660-666.
113. (d) Domingo, L. R.; Aurell, M. J; Pérez, P.; Contreras, R. J. Phys. Chem. A 2002, 106, 6871-6875.
114. Domingo, L. R.; Aurell, M. J.; Pérez, P.; Contreras, R. Tetrahedron 2002, 58, 4417-4423.
115. A detailed study on the geometric and electronic features of HTAD can be found in: Anas, S.; Krishnan, K. S.; Sajisha, V. S.; Anju, K. S.; Radhakrishnan, K. V.; Suresh, E.; Suresh, C. H. New J. Chem. 2007, 31, 237-246.
116. Compare with the values of the global electrophilicity indexes of strong electrophiles in ref 48.
117. (a) Hegarty, D.; Robb, M. A. Mol. Phys. 1979, 38, 1795-1812.
118. (b) Eade, R. H. E.; Robb, M. A. Chem. Phys. Lett. 1981, 83, 362-368.
119. (c) Schlegel, H. B.; Robb, M. A. Chem. Phys. Lett. 1982, 93, 43-46.
120. Hudson, R. F.; Chopard, P. A. J. Org. Chem. 1963, 28, 2446-2447.
121. Thiazole 7a was obtained with minor impurities after purification by column chromatography. It was used for the next step without further purification. The NMR spectra shown in the Supporting Information were obtained from a first fraction obtained in a second chromatography.