Isolation and characterization of 2-alkylaminobenzo[b]furans. Evidence for competing O-arylation in Cu-catalyzed intramolecular amidation

Tetrahedron Letters

Volumn 48, Issue 3, 2007, Pages 401-404

  Feng, Gaofeng ^a   Wu, Jinlong ^a   Dai, Wei Min ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

2 Oxindole; Amidation; Benzo b furan; Cu catalysis

Indexed keywords

ALKYL GROUP; AMIDE; BENZOFURAN DERIVATIVE; COPPER; NITROGEN;

AMIDATION; ARTICLE; ARYLATION; CATALYSIS; COMPLEX FORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; ISOLATION PROCEDURE; MICROWAVE COOKING; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 33845411956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.084     Document Type: Article

References (27)

1. For selected recent reviews, see:. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400-5449
2. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428-2439
3. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337-2364
4. Ullmann F. Ber. Dtsch. Chem. Ges. 36 (1903) 2382-2384
5. Goldberg I. Ber. Dtsch. Chem. Ges. 39 (1906) 1691-1692
6. Pan X., Cai Q., and Ma D. Org. Lett. 6 (2004) 1809-1812
7. Deng W., Wang Y.-F., Zou Y., Liu L., and Guo Q.-X. Tetrahedron Lett. 45 (2004) 2311-2315
8. Yang T., Lin C., Fu H., Jiang Y., and Zhao Y. Org. Lett. 7 (2005) 4781-4784
9. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
10. Klapars A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421-7428 and references cited therein
11. Huang X., Anderson K.W., Zim D., Jiang L., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 6653-6655
12. Wolter M., Klapars A., and Buchwald S.L. Org. Lett. 3 (2001) 3803-3805
13. Han C., Shen R., Su S., and Porco Jr. J.A. Org. Lett. 6 (2004) 27-30
14. For successful examples of Pd-catalyzed intramolecular amidation of N-cyclcohexyl carboxamides, see:. van den Hoogenband A., den Hartog J.A.J., Lange J.H.M., and Terpstra J.W. Tetrahedron Lett. 45 (2004) 8535-8537
15. Xing X., Wu J., and Dai W.-M. Synlett (2006) 2099-2103
16. Poondra R.R., and Turner N.J. Org. Lett. 7 (2005) 863-866
17. Bonnaterre F., Bois-Choussy M., and Zhu J. Org. Lett. 8 (2006) 4351-4354
18. For a failed example of Pd-catalyzed intramolecular amidation of N-t-butyl carboxamide, see:. Kalinski C., Umkehrer M., Ross G., Kolb J., Burdack C., and Hiller W. Tetrahedron Lett. 47 (2006) 3423-3426
19. Yin J., and Buchwald S.L. Org. Lett. 2 (2000) 1101-1104
20. For an example of Cu-catalyzed intramolecular O-arylation of ortho-halobenzanilides, see:. Evindar G., and Batey R.A. J. Org. Chem. 71 (2006) 1802-1808
21. Xinglong X., Wu J., Feng G., and Dai W.-M. Tetrahedron 62 (2006) 6774-6781
22. Lang J.H.M., Hofmeyer L.J.F., Hout F.A.S., Osnabrug S.J.M., Verver P.C., Kruse C.G., and Feenstra R.W. Tetrahedron Lett. 43 (2002) 1101-1104
23. Wannberg J., Dallinger D., Kappe C.O., and Larhed M. J. Comb. Chem. 7 (2005) 574-583
24. 2-Alkylaminobenzo[b]furans were synthesized from ammonium formate, 2-hydroxybenzaldehyde, and alkylisocyanides, see:. Bossio R., Marcaccini S., Paoli P., Pepino R., and Polo C. Synthesis (1991) 999-1000
25. The crystallographic data (excluding structure factors) of 2d, 3e and 9b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 612701, CCDC 612702, and CCDC 612703, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
26. Oxidative cleavage of an electron-rich benzo[b]furan by singlet oxygen is known, see:. Adam W., Kades E., and Wang X. Tetrahedron Lett. 31 (1990) 2259-2262
27. 15{A figure is presented}