Microwave enhanced tandem 5-exo cyclization/Claisen rearrangement reactions: A convenient route to cycloheptanoid ring systems

Synlett

Volumn , Issue 14, 2004, Pages 2579-2581

  McIntosh, Caitlin E ^a   Martínez, Isamir ^a   Ovaska, Timo V ^a  

^a The Holleran Center for Community Action and Public Policy   (United States)

Author keywords

5 exo cyclization; Claisen rearrangement; Microwave irradiation; Solvent free

Indexed keywords

2 METHYLENETETRAHYDROFURAN DERIVATIVE; ALKYNE DERIVATIVE; BASE; CARBENE; CYCLOHEPTANE DERIVATIVE; CYCLOHEPTANOID DERIVATIVE; SOLVENT; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; CONFORMATIONAL TRANSITION; CYCLIZATION; GAS CHROMATOGRAPHY; HEATING; MICROWAVE IRRADIATION; REACTION ANALYSIS; REPRODUCIBILITY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE; THIN LAYER CHROMATOGRAPHY;

EID: 9644275359     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834790     Document Type: Article

References (18)

1. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L. Tetrahedron Lett. 1986, 27, 279.
2. See, for example: (a) Perreaux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
3. (b) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
4. (c) Caddick, S. Tetrahedron 1995, 51, 10403.
5. For recent examples, see: (a) Schobert, R.; Gordon, G. J.; Mullen, G.; Stehle, R. Tetrahedron Lett. 2004, 45, 1121.
6. (b) Yamamoto, T.; Wada, Y.; Enokida, H.; Fujimoto, M.; Nakamura, K.; Yanagida, S. Green Chem. 2003, 5, 690.
7. (c) Kumar, H. M. S.; Anjaneylu, S.; Reddy, B. V. S.; Yadav, J. S. Synlett 2000, 1129.
8. Durand-Reville, T.; Gobbi, L. B.; Gray, B. L.; Ley, S. V.; Scott, J. S. Org. Lett. 2002, 4, 3847.
9. Marvell, E. N.; Titterington, D. Tetrahedron Lett. 1980, 2123.
10. Ovaska, T. V.; Roark, J. L.; Shoemaker, C. M. Tetrahedron Lett. 1998, 39, 5705.
11. Ovaska, T. V.; Roses, J. B. Org. Lett. 2000, 2, 2361.
12. Ovaska, T. V.; Ravi Kumar, J. S.; Hulford, C. A.; O'Sullivan, M. F.; Reisman, S. E. Tetrahedron Lett. 2002, 43, 1939.
13. Ovaska, T. V.; Reisman, S. E.; Flynn, M. A. Org. Lett. 2001, 3, 115.
14. CEM Discover Focused Microwave™ Synthesis System was used for all reactions.
15. Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
16. 2O and the tube was placed in the microwave oven for the specified time. The product mixture was then either chromatographed on silica gel directly (when phenetole was used as the solvent) or following removal of the solvent and aqueous work-up (when DMF was used as the solvent).
17. All previously reported compounds gave spectroscopic and analytical results consistent with their assigned structures.
18. Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Carte, B.; Jurewicz, A. J.; Johnson, R. K. Tetrahedron 1997, 53, 5047.