Microwave-assisted solid-phase synthesis of 5-carboxamido-N-acetyltryptamine derivatives

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2613-2615

  Fînaru, Adriana ^a   Berthault, Aurélie ^a   Besson, Thierry ^a,b   Guillaumet, Gérald ^a   Berteina Raboin, Sabine ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b UNIVERSITÉ DE LA ROCHELLE   (France)

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ARTICLE;

EID: 0000333337     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0259185     Document Type: Article

References (22)

1. For a discussion, see: (a) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2001, ASAP article.
2. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1997, 53, 5643-5678.
3. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
4. Stadler, A.; Kappe, C. O. Eur. J. Org. Chem. 2001, 919-925 and references therein.
5. The most cited reviews (more than 100 citations) in microwave-assisted chemistry (Science Citation Index, August 2001): (a) Caddick, S. Tetrahedron 1995, 51, 10403-10432.
6. (b) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1233.
7. (c). Varma, R. S. Green Chem. 1999, 43-55.
8. (a) Yu, H.-M.; Chen, S. T.; Wang, K. T. J. Org. Chem. 1992, 57, 7, 4781-4784.
9. (b) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219-8222.
10. (c) Kuster, G.; Scheeren, H. W. Tetrahedron Lett. 2000, 41, 515-519.
11. (d) Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett. 1999, 40, 3941-3944.
12. (e) Strohmeier, G. A.; Kappe, C. O. J. Comb. Chem. 2002, 4, 154-161.
13. (f) Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623-1626.
14. Fînaru, A.; Berthault, A.; Besson, T.; Guillaumet, G.; Berteina-Raboin, S. Tetrahedron Lett. 2002, 43, 787-790.
15. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
16. The Rink resin had previously been used in microwave-assisted solid-phase chemistry; see ref 5f.
17. Focused microwave irradiations were carried out at atmospheric pressure with a Synthewave S402 Prolabo microwave reactor (300 W, monomode system), which has quartz reactors, visual control, irradiation monitored by PC computer, infrared measurement, and continuous feedback temperature control (Commarmot, R.; Didenot, R.; Gardais, J. F. French Patent 84/03496, 1986; Chem. Abst. 1986, 105, 17442.)
18. Focused microwave irradiations were carried out at atmospheric pressure with a Synthewave S402 Prolabo microwave reactor (300 W, monomode system), which has quartz reactors, visual control, irradiation monitored by PC computer, infrared measurement, and continuous feedback temperature control (Commarmot, R.; Didenot, R.; Gardais, J. F. French Patent 84/03496, 1986; Chem. Abst. 1986, 105, 17442.)
19. N-[4-(1,1,1-Trimethylsily)-3-butyn-1-yl]acetamide 3 was obtained, in six steps, from commercially available but-3-ynol (see ref 7).
20. (a) Ujjainwalla, F.; Warner, D. Tetrahedron Lett. 1998, 39, 5355-5358.
21. (b) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690.
22. 1H NMR (250 MHz) and mass spectroscopy.