A practical and efficient intramolecular Michael addition of ureas to α,ab-unsaturated esters

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1147-1150

  Xin, Zhili ^a   Pei, Zhonghua ^a   Von Geldem, Tom ^a   Jirousek, Michael ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Cyclization; Dihydroquinazolines; Michael addition; Ureas

Indexed keywords

ESTER DERIVATIVE; QUINAZOLINE DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034685298     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02283-2     Document Type: Article

References (13)

1. (a) Bergman, E. D.; Ginsberg, D.; Rappo, R. Org. React. 1959, 10, 179.
2. (b) House, H. O. Modern Synthetic Reactions; Benjamin: Menlo Park, California, 1972; pp. 595-623.
3. Cabral, J.; Laszlo, P.; Mahe, L.; Montaufier, M. T.; Randriamahefa, S. L. Tetrahedron Lett. 1989, 30, 3969.
4. Ahn, K. M.; Lee, S. J. Tetrahedron Lett. 1994, 35, 1875.
5. (a) Maggini, M.; Prato, M.; Ranelli, M.; Scorrano, G. Tetrahedron Lett. 1992, 33, 6537.
6. (b) Fang, F. G.; Prato, M.; Kim, G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 3625.
7. Molina, P.; Aller, E.; Lorenzo, A. Synthesis, 1998, 283.
8. Saito, T.; Tsuda, K.; Saito, Y. Tetrahedron Lett. 1996, 37, 209.
9. Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
10. Bordwell, F. C. Acc. Chem. Res. 1988, 21, 456.
11. 13C correlation to C15 (δ=140.7 ppm) indicating that the phenyl group is attached to the N next to C7 as shown here:
12. Papadopoulos, E. P.; Torres, C. D. J. Heterocyclic Chem. 1982, 19, 269.
13. Baldwom, J. E. J. Chem. Soc., Chem. Commum. 1976, 734.