Cycloadditions of 1,5- and 1,7-azulenequinones to benzo[c]furan and its 1,3-diphenyl derivative

Heterocycles

Volumn 43, Issue 3, 1996, Pages 527-530

  Takeshita, Hitoshi ^a   Yan, Yong Zhe ^a   Mori, Akira ^a   Nozoe, Tetsuo ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b KAO CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005808625     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-7350     Document Type: Article

References (9)

1. L. T. Scott and C. M. Adams, J. Am. Chem. Soc., 1984, 106, 4857.
2. The term, [m+n], denotes the mode of the reaction between mit of AQ and nπ of the counterpart.
3. T. Nozoe, H. Takeshita, Y. Z. Yan, and A. Mori, Synlett, 1995, 375.
4. H. Takeshita, Y. Z. Yan, N. Kato, A. Mori, and T. Nozoe, Tetrahedron Lett., 1995, 36, 5195.
5. H. Takeshita, Y. Z. Yan, N. Kato, A. Mori, T. Wakabayashi, and T. Nozoe, Tetrahedron Lett., 1995, 36, 5199.
6. The AQ hitherto isolated are only derivatives having no cyclopentadienone moiety. See e.g., M. Morita and K. Takase, Chem. Lett., 1978, 513; Y. Matsubara, H. Yamamoto, and T. Nozoe, "Studies on Natural Product Chemistry", Vol. 14, ed. by Atta-ur-Rahman, Elsevier, Amsterdam, 1994, pp.313-354.
7. The AQ hitherto isolated are only derivatives having no cyclopentadienone moiety. See e.g., M. Morita and K. Takase, Chem. Lett., 1978, 513; Y. Matsubara, H. Yamamoto, and T. Nozoe, "Studies on Natural Product Chemistry", Vol. 14, ed. by Atta-ur-Rahman, Elsevier, Amsterdam, 1994, pp.313-354.
8. One shoud notice that stereospecific formation of 1 from DIBF and 5-AQ is attributable to the conjugated nature of [1,5] sigmatropy and second [2+4] cycloaddition step; others, all 1:2-cycloadduct formations are non-stereospecific.
9. S. Itô, K. Sakan, and Y. Fujise, Tetrahedron Lett., 1969, 775.