The annulation of 3-alkylindoles with 1,1-cyclopropanediesters

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5671-5675

  Kerr, Michael A ^a,b   Keddy, Ryan G ^a  

^a ACADIA UNIVERSITY   (Canada)

^b UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; METHYL GROUP;

ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; REACTION TIME; STEREOSPECIFICITY; SYNTHESIS; THERMAL EXPOSURE;

EID: 0033618302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01107-7     Document Type: Article

References (15)

1. Harrington, P. E.; Kerr, M. A. Tetrahedron Lett. 1997, 38, 5949-5952.
2. Garnick, R. L.; Levery, S. B.; Le Quesne, P. W. J. Org. Chem. 1978, 43, 1226-1229.
3. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364.
4. 3 (5 mol%) were weighed into a dry reaction vessel, equipped with a stirring bar. The vessel was then purged with argon under a septum seal. Acetonitrile was added via syringe and the mixture stirred for the indicated period of time at either room temperature, reflux or in a sealed tube. When TLC analysis of the reaction mixture indicated that the reaction progress had ceased, the mixture was brought to ambient temperature and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel using mixtures of EtOAc/hexane as the eluant. High pressure-the reaction mixture was prepared as in Method A and was transferred to a length of heat shrinkable teflon tubing which was sealed at one end with a brass clamp. Excess air was squeezed from the tubing and it was sealed with a second clamp. The tubing was inserted into the high pressure reactor and the pressure increased to 13 kbar. After the indicated period of time, the reactor was depressurized and the reaction mixture transferred to a round-bottomed flask and worked up in the usual way.
5. 4, found: 331.1779 amu, requires: 331.1783 amu.
6. Jackson, A. H.; Naidoo, B.; Smith, P. Tetrahedron 1968, 24, 6119-6129.
7. (a) Charette, A. B.; Juteau, H.; Lebel, H.; Deschenes, D. Tetrahedron Lett. 1996, 37, 7925-7928.
8. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081-1083.
9. (c) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651-2652.
10. (d) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897-6907.
11. For an excellent leading article, see: C & EN News, June 16, 1997; p. 32.
12. (a) Didier, E.; Loubinoux, B.; Ramos-Tombo, G. M.; Rihs, G. Tetrahedron 1991, 47, 4941.
13. (b) Kim, Y. H.; Park, D. H.; Byun, I. S.; Yoon, I. K.; Park, C. S. J. Org. Chem. 1993, 58, 4511-4512.
14. (c) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Shing, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926.
15. (d) For a review of this topic, see: Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784.