Periselective [4π+2π] cycloaddition reactions of 3-ethoxy carbonyl-2H-cyclohepta[b]furan-2-one with aralkenes

Chemistry Letters

Volumn , Issue 6, 1997, Pages 505-506

  Nair, Vijay ^a   Nair, Anilkumar G ^a   Rath, Nigam P ^b   Eigendorf, Guenter K ^c  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011219430     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.505     Document Type: Article

References (31)

1. a) J. H. Rigby, In Comprehensive organic Synthesis, ed by B. M. Trost, and I. Fleming, Pergamon Press, Oxford, (1991), Vol. 5, pp.617-643.
2. b) J. H. Rigby, Acc. Chem. Res., 26, 579 (1990).
3. a) P. W. Yang, M. Yasunami, and K. Takase, Tetrahedron Lett., 45, 4275 (1971).
4. b) A. Chen, M. Yasunami, and K. Takase, Tetrahedron Lett., 30, 2581 (1974).
5. c) M. Yasunami, P.W. Yang, Y. Kondo, Y. Noro, and K. Takase, Chem. Lett., 1980, 167,
6. d) M. Yasunami, A. Chen, P. W. Yang, and K. Takase, Chem. Lett., 1980, 579.
7. e) M. Yasunami, A. Chen, Y. Noro, and K. Takase, Chem.Lett., 1981, 555.
8. f) H. Fujimori, T. Fujita, K. Yamane, M. Yasunami, and K. Takase, Chem. Lett., 1983, 1721.
9. g) S. Kuroda, S. Hirooka, H. Iwaki, M. Ikeda, T. Nakao, M. Obisu, M. Yasunami, and K. Takase, Chem. Lett., 1986, 2039.
10. h) S. Kuroda, M. Mouri, K. Hayashi, M. Oda, (the Late) M. Yamada, I. Shimao, H. Osaki, and M. Yasunami, Chem. Lett., 1994, 85.
11. i) K. Ito, H. Kawaji, and M. Nitta, Tetrahedron Lett., 35, 2561 (1994).
12. j) Y. Kitamori, M. Yasunami, C. Kabuto, and K. Takase, Bull.Chem. Soc. Jpn., 66, 245 (1993).
13. k) M. Yasunami, S. Miyoshi, N. Kanegae, and K. Takase, Bull. Chem. Soc. Jpn., 66, 892 (1966).
14. l) M. Yasunami, T. Hioki, Y. Kitamori, I. Kikuchi, and K. Takase, Bull. Chem Soc. Jpn., 66, 2273 (1993).
15. a) T. Nozoe, P. W. Yang, C. P. Wu, T. S. Huang, T. H. Lee, H. Okai, H. Wakabayashi, and S. Ishikawa, Heterocycles, 29, 1225 (1989).
16. b) T. Nozoe, H Wakabayashi, S. Ishikawa, C. P. Wu, and P. W. Yang, Heterocycles, 31, 17 (1990).
17. c) T. Nozoe, H. Wakabayashi, K. Shindo, S. Ishikawa, C. P. Wu, and P. W. Yang, Heterocycles, 32, 213 (1991).
18. a) A Mori, Y. Nukkii, H. Takeshita, and T. Nozoe, Heterocycles, 35, 863 (1993).
19. b) M. Yasunami, Y. Kitamori, I. Kikuchi, H. Ohmi, and K. Takase, Bull. Chem. Soc. Jpn, 65, 2127 (1992).
20. c) H. Tomioka and M. Nitta, Heterocycles, 38, 629 (1993).
21. There is one report in which the [4π+2π] cycloaddition of cyclo heptafuranone with the Diels-Alder adduct of furan and DMAD has been observed. G. R. Tian, S. Sugiyama, A. Mori, H. Takeshita, M. Higashi, and H. Yamaguchi, Chem. Lett., 1988, 941.
22. a) V. Nair, S. Kumar, and P. G. Williard, Tetrahedron Lett., 35, 1605 (1995).
23. b) V. Nair and S. Kumar, Tetrahedron, 52, 4029 (1996).
24. c) V. Nair, S. Kumar, G. Anilkumar, and J. S Nair, Tetrahedron, 51, 9155, (1995).
25. d) Review. V. Nair and S. Kumar, Synlett, 1996, 1143.
26. The cycloadditions of electron rich heptafulvenes have been investigated in detail. A. Hasehundle, K. M. Rapp and J. Daub, Chem. Lett., 1979, 597 and references cited therein.
27. Typical Experimental procedure. 3-Ethoxycarbonyl-2H-cyclohepta[b]-furan-2-one (109 mg, 0.5 mmol) and acenaphthylene (229 mg, 1.5 mmol) were dissolved in dry toluene (0.5 ml) in a Schlenk glass tube and it was sealed under nitrogen and heated at 160 °C for 20 h. When all the dienophile was reacted (as indicated by tlc), the reaction mixture was chromatographed on silica gel column. Elution with 5% ethyl acetate in hexane afforded 3 and 4 (57.3%) in 1.2 : 1 ratio. The unreacted cyclohepta[b]furan-2-one (33%) was recovered by elution with 30% ethyl acetate in hexane. The products were crystallised from dichloromethane/hexane mixture as colourless crystals.
28. 3 δ: 168.47, 166.45, 160.86, 148.55, 143.57, 140.25, 140.00, 133.50, 132.84, 131.42, 128.17, 127.76,124.06, 123.54, 121.67, 120.37,118.30, 113.53, 87.89, 61.01, 52.68, 46.65, 41.27, 13.96. Analysis: Found C-77.85%, H-4.88% (calculated C 77.82%, H-4.89%)
29. -1. Reflections collected = 18592. Strucure solution and refinement were carried out using SHELXTL-PLUS (5.03) software package (Sheldrick, G. M, Siemens Analytical X-ray Division, Madison, WI 1995).
30. a) M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899 (1977).
31. b) M. J. S Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4907 (1977).