Intramolecular formal Diels-Alder reaction in enyne allenes. A new synthetic route to benzofluorenes and indeno[1,2-g]quinolines

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 999-1002

  Schmittel, Michael ^a   Strittmatter, Marc ^a   Vollmann, Karl ^a   Kiau, Susanne ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENE DERIVATIVE; INDENE DERIVATIVE; INDENO[1,2 G]QUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030040526     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02369-0     Document Type: Article

References (32)

1. Thermal and electron transfer induced reactions of enediynes and enyne allenes, part 3; for part 2 see M. Schmittel, S. Kiau, Chem. Lett. 1995, 953-954.
2. For reviews, see: M. E. Maier, Synlett 1995, 13-26. - K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416.
3. For reviews, see: M. E. Maier, Synlett 1995, 13-26. - K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416.
4. For reviews, see: M. E. Maier, Synlett 1995, 13-26. - K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416.
5. K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875-8876. - T. Takahashi, Y. Sakamoto, H. Yamada, S. Usui, Y. Fukazawa, Angew. Chem. 1995, 107, 1443-1446; Angew. Chem. Int. Ed. Engl. 1995, 43, 1345-1348. - K. Yoshida, Y. Minami, T. Otani, Y. Tada, M. Hirama, Tetrahedron Lett. 1994, 35, 5253-5256. - K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825-7826. - A. G. Myers, Tetrahedron Lett. 1987, 28, 4493-4496.
6. K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875-8876. - T. Takahashi, Y. Sakamoto, H. Yamada, S. Usui, Y. Fukazawa, Angew. Chem. 1995, 107, 1443-1446; Angew. Chem. Int. Ed. Engl. 1995, 43, 1345-1348. - K. Yoshida, Y. Minami, T. Otani, Y. Tada, M. Hirama, Tetrahedron Lett. 1994, 35, 5253-5256. - K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825-7826. - A. G. Myers, Tetrahedron Lett. 1987, 28, 4493-4496.
7. K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875-8876. - T. Takahashi, Y. Sakamoto, H. Yamada, S. Usui, Y. Fukazawa, Angew. Chem. 1995, 107, 1443-1446; Angew. Chem. Int. Ed. Engl. 1995, 43, 1345-1348. - K. Yoshida, Y. Minami, T. Otani, Y. Tada, M. Hirama, Tetrahedron Lett. 1994, 35, 5253-5256. - K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825-7826. - A. G. Myers, Tetrahedron Lett. 1987, 28, 4493-4496.
8. K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875-8876. - T. Takahashi, Y. Sakamoto, H. Yamada, S. Usui, Y. Fukazawa, Angew. Chem. 1995, 107, 1443-1446; Angew. Chem. Int. Ed. Engl. 1995, 43, 1345-1348. - K. Yoshida, Y. Minami, T. Otani, Y. Tada, M. Hirama, Tetrahedron Lett. 1994, 35, 5253-5256. - K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825-7826. - A. G. Myers, Tetrahedron Lett. 1987, 28, 4493-4496.
9. K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875-8876. - T. Takahashi, Y. Sakamoto, H. Yamada, S. Usui, Y. Fukazawa, Angew. Chem. 1995, 107, 1443-1446; Angew. Chem. Int. Ed. Engl. 1995, 43, 1345-1348. - K. Yoshida, Y. Minami, T. Otani, Y. Tada, M. Hirama, Tetrahedron Lett. 1994, 35, 5253-5256. - K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825-7826. - A. G. Myers, Tetrahedron Lett. 1987, 28, 4493-4496.
10. K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875-8876. - T. Takahashi, Y. Sakamoto, H. Yamada, S. Usui, Y. Fukazawa, Angew. Chem. 1995, 107, 1443-1446; Angew. Chem. Int. Ed. Engl. 1995, 43, 1345-1348. - K. Yoshida, Y. Minami, T. Otani, Y. Tada, M. Hirama, Tetrahedron Lett. 1994, 35, 5253-5256. - K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825-7826. - A. G. Myers, Tetrahedron Lett. 1987, 28, 4493-4496.
11. J. W. Grissom, D. Huang, Angew. Chem. 1995, 107, 2196-2198; Angew. Chem., Int. Ed. Engl. 1995, 34, 2037-2039. - J. W. Grissom, B. J. Slattery, Tetrahedron Lett. 1994, 35, 5137-5410. - J. W. Grissom, D. Huang, J. Org. Chem. 1994, 59, 5114-5116. - Y. W. Andemichael, Y. G. Gu, K. K. Wang, J. Org. Chem. 1992, 57, 794 -796. - Y. W. Andemichael, Y. Huang, K. K. Wang, J. Org. Chem. 1993, 58, 1651-1652.
12. J. W. Grissom, D. Huang, Angew. Chem. 1995, 107, 2196-2198; Angew. Chem., Int. Ed. Engl. 1995, 34, 2037-2039. - J. W. Grissom, B. J. Slattery, Tetrahedron Lett. 1994, 35, 5137-5410. - J. W. Grissom, D. Huang, J. Org. Chem. 1994, 59, 5114-5116. - Y. W. Andemichael, Y. G. Gu, K. K. Wang, J. Org. Chem. 1992, 57, 794 -796. - Y. W. Andemichael, Y. Huang, K. K. Wang, J. Org. Chem. 1993, 58, 1651-1652.
13. J. W. Grissom, D. Huang, Angew. Chem. 1995, 107, 2196-2198; Angew. Chem., Int. Ed. Engl. 1995, 34, 2037-2039. - J. W. Grissom, B. J. Slattery, Tetrahedron Lett. 1994, 35, 5137-5410. - J. W. Grissom, D. Huang, J. Org. Chem. 1994, 59, 5114-5116. - Y. W. Andemichael, Y. G. Gu, K. K. Wang, J. Org. Chem. 1992, 57, 794 -796. - Y. W. Andemichael, Y. Huang, K. K. Wang, J. Org. Chem. 1993, 58, 1651-1652.
14. J. W. Grissom, D. Huang, Angew. Chem. 1995, 107, 2196-2198; Angew. Chem., Int. Ed. Engl. 1995, 34, 2037-2039. - J. W. Grissom, B. J. Slattery, Tetrahedron Lett. 1994, 35, 5137-5410. - J. W. Grissom, D. Huang, J. Org. Chem. 1994, 59, 5114-5116. - Y. W. Andemichael, Y. G. Gu, K. K. Wang, J. Org. Chem. 1992, 57, 794 -796. - Y. W. Andemichael, Y. Huang, K. K. Wang, J. Org. Chem. 1993, 58, 1651-1652.
15. J. W. Grissom, D. Huang, Angew. Chem. 1995, 107, 2196-2198; Angew. Chem., Int. Ed. Engl. 1995, 34, 2037-2039. - J. W. Grissom, B. J. Slattery, Tetrahedron Lett. 1994, 35, 5137-5410. - J. W. Grissom, D. Huang, J. Org. Chem. 1994, 59, 5114-5116. - Y. W. Andemichael, Y. G. Gu, K. K. Wang, J. Org. Chem. 1992, 57, 794 -796. - Y. W. Andemichael, Y. Huang, K. K. Wang, J. Org. Chem. 1993, 58, 1651-1652.
16. J. W. Grissom, D. Huang, Angew. Chem. 1995, 107, 2196-2198; Angew. Chem., Int. Ed. Engl. 1995, 34, 2037-2039. - J. W. Grissom, B. J. Slattery, Tetrahedron Lett. 1994, 35, 5137-5410. - J. W. Grissom, D. Huang, J. Org. Chem. 1994, 59, 5114-5116. - Y. W. Andemichael, Y. G. Gu, K. K. Wang, J. Org. Chem. 1992, 57, 794 -796. - Y. W. Andemichael, Y. Huang, K. K. Wang, J. Org. Chem. 1993, 58, 1651-1652.
17. R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990 , 31, 2907-2910 - A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057-8059.
18. R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990 , 31, 2907-2910 - A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057-8059.
19. In our model systems the ene functionality is replaced by a phenyl group.
20. M. Schmittel, M. Strittmatter, S. Kiau, Tetrahedron Lett. 1995, 36, 4975-4978.
21. For intermolecular ene-reaction of allenes and acetylenes, see H.-A. Chia, B. E. Kirk, D. R. Taylor, J. Chem. Soc., Perkin Trans. 1 1974, 1209-1213.
22. J. E. Bennett, J. A. Howard, Chem. Phys. Lett. 1971, 9, 460.
23. So far, only indirect proof for the biradical cyclization could be obtained: M. Schmittel, M. Strittmatter, S. Kiau, J. Am. Chem. Soc., manuscript in preparation.
24. -1) 2208 (C=C), 1928 (C=C=C), 1632 (C=N).
25. 3) δ 3.28 (s, 2H).
26. Since an intramolecular 1,5-hydrogen shift is highly unlikely, we suggest that this reaction is taking place via an intermolecular H-addition /abstraction mechanism in between two molecules of 3 or in between 3 and the the added hydrogen donor. R. L. Danheiser, A. E. Gould, R. F. de la Pradilla, A. L. Helgason, J. Org. Chem. 1994, 59, 5514-5515.
27. The two rotational isomers could be separated by chromatography allowing to unequivocally establish their structures on the basis of their spectral data.
28. A biradical B (scheme 3) or alternatively a Zwitterion are thought to constitute the postulated intermediate in the formal Diels-Alder reaction.
29. 8 biradical cyclization has been reported by S. W. Scheuplein, R. Machinek, J. Suffert, R Brückner, Tetrahedron Lett. 1993, 34, 6549-6552.
30. In concerted Diels-Alder reactions ortho substituents are usually prohibitive, see R Brückner, R. Huisgen, J Schmid. Tetrahedron Lett. 1990, 31, 7129-7132.
31. To the best of our knowledge thermal cyclizations of enyne allenes carrying aryl or vinyl groups at the alkine terminus are not reported in the literature, although for few examples the synthesis was reported: K. K. Wang, Z. Wang, Tetrahedron Lett. 1994, 35, 1829-1832. - K. K. Wang, J. Chin. Chem. Soc. 1995, 42, 745-749.
32. To the best of our knowledge thermal cyclizations of enyne allenes carrying aryl or vinyl groups at the alkine terminus are not reported in the literature, although for few examples the synthesis was reported: K. K. Wang, Z. Wang, Tetrahedron Lett. 1994, 35, 1829-1832. - K. K. Wang, J. Chin. Chem. Soc. 1995, 42, 745-749.