Synthesis and reactions of a novel furo[3,4-d]oxazole

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7680-7686

  Reck, Stephan ^a   Friedrichsen, Willy ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000949277     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980505w     Document Type: Article

References (101)

1. (a) Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5.
2. (b) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87.
3. Dean, F. M. Adv. Heterocyd. Chem. 1981, 30, 168.
4. (a) Friedrichsen, W.; Pagel, K. Progress in Heterocydic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1995; Vol. 7.
5. (b) Reck, S.; Friedrichsen, W. Progress in Heterocydic Chemistry; Suschitzky, H., Gribble, G. W., Eds.; Pergamon Press: Oxford, 1996; Vol. 8.
6. Reck, S.; Friedrichsen, W. Progress in Heterocydic Chemistry; Suschitzky, H., Gilchrist, T. L., Eds.; Pergamon Press: Oxford, 1997; Vol. 9.
7. (a) Peters, O.; Friedrichsen, W. Trends Heterocyd. Chem.; 1995, 4, 217.
8. (b) Elderiield, R. C. Heterocydic Chemistry; Elderfield, R. C., Ed.; Wiley: New York 1951; Vol. 2; p 68.
9. (c) Haddadin, M. J. Heterocydes 1978, 9, 865.
10. (d) Sargent, M. V.; Cresp, T. M. Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 4; p 693.
11. (e) Friedrichsen, W. Adv. Heterocyd. Chem. 1980,26,135.
12. (f) Wiersuni, U. E. Aldrichimica Acta 1981,14, 53.
13. (g) Dean, F. M.; Sargent, M. V.; Comprehensive Heterocydic Chemistry; Katritzky, A. R., Rees, C. W., Eds; Pergamon Press: Oxford, 1984; Vol. 4, p 531.
14. (h) Sargent, M. V.; Dean, F. M. Comprehensive Heterocydic Chemistry; Katritzky, A. R., Rees, C. W., Eds; Pergamon Press: Oxford, 1984; Vol. 4; p 599.
15. Donnelly, D. M. X.; Meegan, M. J. Comprehensive Heterocydic Chemistry; Katritzky, A. R., Rees, C. W., Eds; Pergamon Press: Oxford, 1984; Vol. 4; p 657.
16. (j) Rodrigo, R. Tetrahedron 1988,44, 2093.
17. (k) Rickborn, B. Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1; p 1.
18. Friedrichsen, W. Methoden Org. Chem. (Houben-Weyi); Kreher, R., Ed.; Thieme Verlag: Stuttgart, 1994; Vol. E6bl, p 163.
19. Friedrichsen, Vf.Adv. Heterocyl. Chem., submitted.
20. (a) Hamer, J. 1,4-Cycloaddilion Reactions; Academic Press: New York, 1967.
21. (b) Wollweber, H. Diels-Alder-Reaktion; Thieme Verlag: Stuttgart, 1972.
22. (c) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10.
23. (d) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63.
24. (e) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P.; Natural Products Synthesis through Pericyclic Reactions; ACS Monograph 180; American Chemical Society: Washington, DC, 1983.
25. (f) Ciganek, E. Org. React. 1984, 32, 1.
26. (g) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984.
27. (h) Fallis, A. G. Can. J. Chem. 1984, 62, 183.
28. Weinrcb, S. M. Ace. Chem. Res. 1985, 18, 16.
29. (j) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
30. (k) Roush, W. R. Advances in Cycloadditions; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2; p 91.
31. (a) Schlicke, B.; Schirmer, H.; Schlüter, A.-D. Adv. Mater. 1995, 7, 544.
32. (b) Kintzel, O.; Münch, W.; Schlüter, A.-D.; Godt, A. J. Org. Chem. 1996, 61, 7304.
33. (b) Meier, H.; Rose, B. Liebigs Ann. /Recueil 1997, 663.
34. (a) Warrener, R. N.; Wang, S.; Russell, R. A. Tetrahedron 1997, 53, 3975.
35. (b) Warrener, R. N.; Wang, S.; Butler, D. N.; Russell, R. A. Synlett 1997, 44.
36. Keay, B. A.; Rodrigo, R. J. Am. Chem. Soc. 1982, 104, 4725.
37. Kende, A. S.; Curran, D. P.; Tsay, Y.; Mills, J. E. Tetrahedron Lett. 1977, 3537.
38. König, B.-M.; Friedrichsen, W. Tetrahedron Lett. 1987,28,4279.
39. Hildebrandt, K; Debaerdemaeker, T.; Friedrichsen, W. Tetrahedron Lett. 1988, 29, 2045.
40. Peters, O.; Friedrichsen, W.; unpublished. Peters, O. Dissertation; University of Kiel, 1996.
41. (a) Peters, O.; Friedrichsen, W. Tetrahedron Lett. 1995, 36, 8581.
42. (b) Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 9285.
43. Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
44. (a) Leong-Neumann, S.; Derrick, S. D.; Dibble, P. W. Tetrahedron Lett. 1995,36,4181.
45. (b) Berkowitz, D. B.; Maeng, J.-H.; Dantzig, A. H.; Shepard, R. L.; Norman, B. H. J. Am. Chem. Soc. 1996, 118, 9426.
46. (c) Berkowitz, D. B.; Maeng, J. H. Tetrahedron: Asymmetry 1996, 7, 1577.
47. (d) Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706.
48. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888.
49. (a) Scheming, A.; Friedrichsen, W. Heterocycles 1986, 24, 307.
50. (b) Scheming, A.; Friedrichsen, W. Tetrahedron Lett. 1988, 29, 1137.
51. (b) Scheming, A.; Friedrichsen, W. Liebigs Ann. Chem. 1989, 405.
52. (c) Scheming, A.; Debaerdemaeker, T.; Zander, M.; Friedrichsen, W. Chem. Ber. 1989, 722,1119.
53. (d) Scheming, A.; Friedrichsen, W. Z. Naturforsch. 1989, 44b, 825.
54. Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166.
55. (a) Assmann, L.; Friedrichsen, W. Heterocycles 1989,29, 1003.
56. (b) Assmann, L.; Debaerdemaeker, T.; Friedrichsen, W. Tetrahedron Lett. 1991, 32,1161.
57. (c) Assmann, L.; Palm, L.; Zander, M.; Friedrichsen, W. Chem. Ber. 1991, 124, 2481.
58. (d) Reck, S.; Bluhm, 1C; Debaerdemaeker, T.; Declercq, J.-P.; Klenke, B.; Friedrichsen, W. Heterocycles 1996, 43, 1165.
59. Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
60. Bussenius, J.; Keller, M.; Eberbach, W. Liebigs Ann. Chem. 1995, 1503.
61. (a) Gribble, G. W.; Saulnier, M. G. J. Chem. Soc., Chem. Comm. 1984, 168.
62. (b) Gribble, G. W.; Saulnier, M. G.; Sibi, M. P.; ObazaNutaitis, J. A. J. Org, Chem. 1984,49,4518.
63. (c) Nagel, J.; Friedrichsen, W.; Debaerdemaeker, T. Z. Naturforsch. 1993,48b, 213.
64. (c) Peters, O.; Friedrichsen, W. Heterocyc. Comm. 1996, 2, 201.
65. Hamaguchi, M.; Ibata, T. Chem. Lett. 1976, 287.
66. Birkhofer, L.; Feldmann, H. Liebigs Ann. Chem. 1964,677,150.
67. Procedure: Treibs, A.; Sutler, W.; Chem. Ber. 1951, 84, 76.
68. The corresponding diethyl ester is known: Vidal-Cros, A. Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163.
69. Review: Turchi, I. J.; Dewar, M. J. S. Chem. Rev. 1975, 75, 389.
70. Review: Regitz, M.; Maas, G. Diazo Compounds. Properties and Synthesis; Academic Press: Orlando, 1986.
71. Hendrickson, J. B.; Wolf, W. A. J. Org. Chem. 1968, 33, 3610.
72. Review: Maas, G. Top. Curr. Chem. 1987, 737, 75.
73. (a) Wittig, G.; Pohlke, R.; Chem. Ber. 1961,94,3276.
74. (b) Wittig, G.; Mayer, U. Chem. Ber. 1963, 96, 329.
75. (c) Wittig, G.; Weinlich, J.; Wilson, E. R. Chem. Ber. 1965, 98, 458.
76. (d) Wittig, G.; Dorsch, H.-L. LiebigsAnn. Chem. 1968, 777, 46.
77. (e) Hildebrandt, K.; Dissertation, University of Kiel, 1988. (0 Cochran J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495.
78. Another type of ring-opening reaction was reported by Hamaguchi and Ibata.23
79. The reaction of furoisoxazoles with DMAD may also yield furooxepines.19
80. The same selectivity was observed in the isoxazole series.19 See also Plug, C.; Friedrichsen, W. J. Chem. Soc., Perkin Trans, l 1996, 1035.
81. (a) Neises, B.; Steglich, W.; Angew. Chem., Int. Ed. Engl. 1978, 77, 552.
82. (a) Hassner, A.; Alexanian, V. Tetrahedron Lett. 1978, 4475.
83. (a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
84. (b) Labanowski, J. K.; Andzelm, J. W. Density Functional Methods in Chemistry; Springer-Verlag: New York, 1991.
85. (c) Ziegler, T. Chem. Rev. 1991,91, 651.
86. (d) Modern Density Functional Theory. A Tool for Chemistry; Seminario, J. M., Politzer, P., Eds.; Elsevier: Amsterdam, 1995.
87. These calculations were performed with the program systems GAUSSIAN9238'39 and GAUSSIAN 94.
88. Gaussian 92, Revision E.2, Frisch, M. J.; Trucks, G. W.; HeadGordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A.; Gaussian, Inc.; Pittsburgh, PA, 1992.
89. Gaussian 92/DFT, Revision G.3, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gorden, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A.; Gaussian, Inc.; Pittsburgh, PA, 1993.
90. Gaussian 94, Revision B.3,-Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S. Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gorden, M.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc.; Pittsburgh, PA, 1995.
91. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
92. Lee, C.; Yang, W.; Pair, G. Phys. Rev. B 1988, 41, 785.
93. Foresman, J. B.; Frisch, M. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.
94. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initia Molecular Orbital Theory; Wiley: New York, 1986.
95. Bauschlicher jun., C. W. Chem. Phys. Lett. 1995, 246, 40.
96. According to all theoretical methods given in Table 1 the furo[3, 4-d]oxazole system is completely planar.
97. Review: Stewart, J. J. P. Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, B. D., Eds.; VCH Publ.: New York, 1990.
98. The program system MOPAC, version 6.0 was used: QCPE Bull. 1992,12, 72.
99. Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P.; J. Org. Chem. 1997, 62, 2786.
100. Jursic, B. S. J. Org. Chem. 1997, 62, 3046.
101. Reck, S.; Näther, C.; Friedrichsen, W. Heterocycles 1998, 48, 853.