Formation of aromatic rings through enamine annulation

Organic Letters

Volumn 2, Issue 12, 2000, Pages 1773-1775

  Wang, Chen ^b   Kohn, Harold ^a,b  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001339915     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000093p     Document Type: Article

References (13)

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2. (b) Chinchilla, R.; Backvall, J. E. The Chemistry of Enamines: Rappoport, Z., Ed.; John & Wiley Sons: New York, 1994; Chapter 18, p 993.
3. (a) Kobayashi, K.; Furuta, Y.; Matsuoka, H.; Uchida, M.; Morikawa, O.; Konishi, H. Chem. Lett. 1999, 6, 503.
4. (b) Murphy, W. S.; Bertrand, M. J. Chem. Soc., Perkin Trans. 1 1998, 4115.
5. (c) Li, J.; Trivedi, B. K.; Rubin, J. R.; Roth, B. D. Tetrahedron Lett. 1998, 39, 6111.
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7. (e) Kao, B. C.; Doshi, H.; Reyes-Rivera, H.; Titus, D. D.; Yin, M.; Dalton, D. R. J. Heterocycl. Chem. 1991, 28, 1315.
8. House, H. O. H.; Trost, B. M.; Magin, R. W.; Carlson, R. G.; Frank, R. W.; Rasmusson, G. H. J. Org. Chem. 1965, 30, 2512.
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10. Compound 8 is unstable in the presence of amines (i.e., pyrrolidine, triethylamine, DBU). 1,7-Diacetoxy-3-methylene-2,6-heptanedione was obtained in 50% yield when a benzene solution of 8 and triethylamine (1 equiv) was stirred at room temperature (1 h).
11. Masamune, T.; Takasngi, M.; Murai, A. Tetrahedron 1971, 27, 3369.
12. Hellberg, L. H.; Milligan, R. J.; Wike, R. N. J. Chem. Soc. C 1970, 35.
13. Gurowitz, W. D.; Joseph, M. A. Tetrahedron Lett. 1965, 3, 4433.