New Access to 2,3-disubstituted Quinolines through Cyclization of o-Alkynylisocyanobenzenes

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1977-1979

  Suginome, Michinori ^a   Fukuda, Takeshi ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

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Indexed keywords

EID: 0000402423     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991133w     Document Type: Article

References (16)

1. For anionic cyclizations, see: Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532. Ito, Y.; Kobayashi, K.; Saegusa, T. Tetrahedron Lett. 1979, 20, 1039. Haefliger, W.; Knecht, H. Tetrahedron Lett. 1984, 25, 289. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
2. For anionic cyclizations, see: Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532. Ito, Y.; Kobayashi, K.; Saegusa, T. Tetrahedron Lett. 1979, 20, 1039. Haefliger, W.; Knecht, H. Tetrahedron Lett. 1984, 25, 289. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
3. For anionic cyclizations, see: Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532. Ito, Y.; Kobayashi, K.; Saegusa, T. Tetrahedron Lett. 1979, 20, 1039. Haefliger, W.; Knecht, H. Tetrahedron Lett. 1984, 25, 289. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
4. For anionic cyclizations, see: Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532. Ito, Y.; Kobayashi, K.; Saegusa, T. Tetrahedron Lett. 1979, 20, 1039. Haefliger, W.; Knecht, H. Tetrahedron Lett. 1984, 25, 289. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
5. For Lewis acid mediated cyclization, see: Ito, Y.; Kobayashi, K.; Saegusa, T. Chem. Lett. 1980, 1563.
6. For radical cyclizations, see: Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. Shinada, T.; Miyachi, M.; Itagaki, Y.; Naoki, H.; Yoshihara, K.; Nakajima, T. Tetrahedron Lett. 1996, 37, 7099.
7. For radical cyclizations, see: Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. Shinada, T.; Miyachi, M.; Itagaki, Y.; Naoki, H.; Yoshihara, K.; Nakajima, T. Tetrahedron Lett. 1996, 37, 7099.
8. Kobayashi, K.; Matoba, T.; Irisawa, S.; Matsumoto, T.; Morikawa, O.; Konishi, H. Chem. Lett. 1998, 551.
9. Synthesis of quinolines by radical reaction of aryl isocyanide with o-alkynyliodobenzenes was reported. See: Josien, H.; Ko, S.-B.; Bom, D.; Curran, D. P. Chem. Eur. J. 1998, 4, 67 and references therein.
10. Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325.
11. A part of this paper was presented at the 76th Chemical Society of Japan National Meeting, March, 1999, Yokohama, 4C303.
12. For the use of 3a in a palladium-mediated cyclization, see: Onitsuka, K.; Segawa, M.; Takahashi, S. Organometallics 1998, 17, 4335.
13. Intermediacy of reactive cyclic allenes was discussed. See: Wills, M. S. B.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9378.
14. One of the reviewers suggested a mechanism involving a initial 6π cyclization of 3, which affords a cyclic allenyl intermediate with a carbene site at the 2-position, followed by trapping with methanol or diethylamine. Although we also considered this alternative mechanism, the mechanism proposed by us may be more likely at this moment, if it is taken into account that each alkynylisocyanobenzene 3 exhibited different reaction rates toward the two different reactants, i.e., methanol and dimethylamine. Indeed, we would expect very similar reaction rate for the two reactions, it the generation of the highly reactive allenyl carbene intermediate is involved in the reaction.
15. Saegusa, T.; Ito, Y. In Isonitrile Chemistry; Ugi, I., Ed.; Academic Press: New York, 1971; p 65.
16. Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.