Intramolecular hetero-Diels-Alder reaction of vinylallenes and imines: Synthesis of 9-methyl-1,2,3,4,5,6,7,8-octahydroacridine

Synthesis

Volumn , Issue 5, 2004, Pages 757-760

  Regás, David ^a   Afonso, María M ^a   Palenzuela, J Antonio ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Cycloaddition; Hetero Diels Alder reaction; Imines; Intramolecular reaction; Vinyl allenes

Indexed keywords

ACIDITY; ACTIVATION ANALYSIS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

INTRAMOLECULAR HETERO-DIELS-ALDER REACTION; LEWIS ACID ACTIVATION;

NITROGEN COMPOUNDS;

ACRIDINE DERIVATIVE; ALKADIENE; ALLENE DERIVATIVE; IMINE; LEWIS ACID;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLOADDITION; DIELS ALDER REACTION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 1942521137     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-816006     Document Type: Article

References (16)

1. The term semicyclic refers to a dienic or vinylallenic system in which only one of the double bonds is a part of a cycle.
2. Regas, D.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron Lett. 2000, 41, 6781.
3. Regas, D.; Afonso, M. M.; Rodríguez, M. L.; Palenzuela, J. A. J. Org. Chem. 2003, 68, 7845.
4. Roush, W. R. Intramolecular Diels-Alder Reactions, In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991, 513-550.
5. (a) Trost, B. M.; Lautens, M.; Hung, M.; Carmichael, C. J. Am. Chem. Soc. 1984, 106, 7641.
6. (b) Rigby, J. Tetrahedron Lett. 1982, 23, 1863.
7. (c) Rigby, J.; Wilson, J. J. Am. Chem. Soc. 1984, 106, 8217.
8. (d)Rigby, J.; Wilson, J.; Senanayake, C. Tetrahedron Lett. 1986, 27, 3329.
9. (e) Snider, B. B.; Liu, T. J. Org. Chem. 2000, 65, 8490.
10. Regas, D.; Ruiz, J. M.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron Lett. 2003, 44, 8471.
11. Okamura, W. H.; Curtin, M. L. Synlett 1990, 1.
12. All compounds described in this paper were prepared in racemic form.
13. (a) Green, T.; Wuts, P. G. M. Protective Groups in Organic Chemistry; Wiley: New York, 1991, 364-366.
14. (b) Midland, M. M.; Afonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368.
15. (a) Pilato, M. L.; Catalano, V. J.; Bell, T. W. J. Org. Chem. 2001, 66, 1525.
16. (b) Kamata, K.; Tominaga, Y.; Tori-i, A.; Thiemann, T.; Matake, S. Hetereocycles 1998, 48, 1663.