Development of a convenient synthetic route to aminochromenes via Buchwald C-N coupling

Tetrahedron Letters

Volumn 48, Issue 23, 2007, Pages 4127-4130

  Shilova, Ekaterina A ^a,b   Perevalov, Valery P ^b   Samat, André ^a   Moustrou, Corinne ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

Author keywords

Aminochromene; Buchwald palladium catalyzed C N coupling; Nitrochromene

Indexed keywords

4 AMINOPHENYLAMINOBENZOPYRAN DERIVATIVE; 4 NITROPHENYLAMINOCHROMENE DERIVATIVE; AMINOCHROMENE DERIVATIVE; CHROMENE DERIVATIVE; NAPHTHOPYRAN DERIVATIVE; PALLADIUM; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; X RAY CRYSTALLOGRAPHY;

EID: 34247889833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.003     Document Type: Article

References (34)

1. In: Dürr H., and Bouas-Laurent H. (Eds). Photochromism: Molecules and Systems (1990), Elsevier, Amsterdam
2. Gemert B.V. Organic Photochromic and Thermochromic Compounds (1999), Plenum Press, New York
3. In: Crano J.C., and Guglielmetti R.J. (Eds). Organic Photochromic and Thermochromic Compounds Vols. 1 and 2 (1999), Kluwer Academic/Plenum Publishers, New York
4. McArdle C.B. Applied Photochromic Systems (1992), Blackie, London
5. Ivaki T., Yasuhara A., and Sakamoto T.J. J. Chem. Soc., Perkin Trans. 1 (1999) 1505-1510
6. Negwer M. Organic Chemical Drugs and their Synonyms (International Survey). 7th ed. (1994), Akademie Verlag Gmbh, Berlin
7. D'Aroano G., Schavion G., and Leclerc M. Chem. Mater. 7 (1995) 33-35
8. Greco G.E., Popa A.I., and Schrock R.R. Organometallics 17 (1998) 5591-5593
9. Ortica F., Moustrou C., Berthet J., Favaro G., Mazzucato U., Samat A., Gugliemetti R., Vermeerch G., and Mazzucato U. Photochem. Photobiol. 78 (2003) 558-566
10. Shilova E.A., Moustrou C., and Samat A. Tetrahedron Lett. 46 (2005) 8857-8859
11. Queiroz M.-J.R.P., Abreu A., Ferreira P.M.T., Oliveira M., Dubest R., Aubard J., and Samat A. Org. Lett. 7 (2005) 4811-4814
12. Muchi A., and Buchwald S. Top. Cur. Chem. 219 (2002) 131-209
13. Wolfe J.P., and Buchwald S.L. Tetrahedron Lett. 38 (1997) 6359-6362
14. Wolfe J.P., Wagaw S., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805-818
15. Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125-146
16. Wolf J.P., and Buchwald S.L. J. Org. Chem. 65 (2000) 1144-1157
17. Bougdid, L. Ph.D. Thesis, Université de la Méditerranée, 2006.
18. Frigoli M., Moustrou C., Samat A., and Gugliemetti R. Eur. J. Org. Chem. (2003) 2799-2812
19. General procedure for the amination reactions: A Schlenk flask was charged with aryl halide (0,9 mmol), amine (1 mmol), sodium tert-butoxide (1.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (2 mol %), 2-(di-t-butylphosphino)biphenyl (4 mol %) in toluene (1 mL/mmol) under argon. The flask was immersed in an 80 °C oil bath with stirring until the starting material had been completely consumed as judged by GC analysis. The solution was then allowed to cool to room temperature, taken up in either and filtered. The solution was concentrated to dryness under reduced pressure. The crude material was purified by column chromatography with cyclohexane-acetone (90:10).
20. 13C NMR (acetone, ppm): δ = 149.4 (1C), 146.2 (1C), 141.4 (1C), 133.9 (1C), 133.3 (1C), 131.7 (1C), 132.6 (1C), 129.3 (1C), 129.1 (1C), 128.9 (4C), 128.2 (2C), 127.6 (4C), 125.5 (1C), 123.4 (1C); 121.5 (1C), 121.2 (1C), 121.1 (1C), 120.7 (2C), 119.3 (2C), 119.2 (2C), 115.5 (1C), 111.3 (1C), 82.7 (1C), 27.5 (1C).
21. + 433, found 433.
22. 13C NMR (acetone, ppm): δ = 150.1 (1C), 147.8 (1C), 146.7 (2C), 144.1 (1C), 143.2 (1C), 136.1 (1C), 129.8 (1C), 129.3 (1C), 128.9 (4C), 128.2 (2C), 127.5 (4C), 127.0 (1C), 126.4 (1C), 123.9 (1C), 122.3 (1C), 121.4 (2C); 120.3 (1C), 116.5 (2C), 81.8 (1C), 27.4 (1C), 15.9 (1C), 13.4 (1C).
23. + 461, found 461.
24. 13C NMR (acetonitrile, ppm): δ = 148.8 (1C), 146.3 (2C), 144.9 (1C), 144.2 (1C), 133.6 (1C), 131.9 (1C), 129.2 (1C), 128.8 (4C), 128.7 (1C), 128.2 (2C), 127.6 (4C); 124.6 (1C), 123.8 (2C), 120.2 (1C), 120.8 (1C), 120.5 (1C), 119.1 (1C), 116.0 (2C), 115.5 (1C), 108.5 (1C), 82.6 (2C).
25. 13C NMR (acetone, ppm): δ = 147.6 (1C), 146.5 (2C), 144.0 (1C), 143.4 (1C), 135.7 (1C), 129.8 (1C), 128.9 (4C), 128.0 (2C), 127.3 (4C), 126.9 (1C), 126.7 (1C), 123.8 (1C), 122.5 (1C), 121.3 (2C), 120.2 (1C), 116.2 (2C), 81.9 (1C).
26. 13C NMR (acetone, ppm): δ = 147.6 (1C), 146.5 (2C), 144.0 (1C), 143.4 (1C), 135.7 (1C), 129.8 (1C), 128.9 (4C), 128.0 (2C), 127.3 (4C), 126.9 (1C), 126.7 (1C), 123.8 (1C), 122.5 (1C), 121.3 (2C); 120.2 (1C), 116.2 (2C), 81.9 (1C), 15.8 (1C), 13.0 (1C).
27. 13C NMR (acetone, ppm): δ = 145.8 (1C), 145.0 (2C), 138.0 (1C), 135.4 (1C), 130.1 (1C), 128.8 (1C), 127.9 (4C), 126.7 (2C), 124.3 (4C), 121.9 (1C), 126.7 (1C), 123.8 (1C), 122.5 (1C), 121.3 (2C), 120.2 (1C), 111.2 (2C), 80.0 (1C), 19.8 (1C), 15.6 (1C).
28. Hydrolysis procedure: Acetanilide (1 mmol) in 10% HCl (30 mL) was stirred at reflux during 30 min, The solution was then allowed to cool to room temperature, 20% NaOH (aqueous) was added until pH 7-8, then the mixture was extracted five times with EtOAc and purified by column chromatography with cyclohexane-acetone (90:10).
29. 13C NMR (acetone, ppm): δ = 151.8 (1C), 150.7 (1C), 145.9 (2C), 139.8 (1C), 136.9 (1C), 130.9 (1C), 129.8 (1C), 129.5 (1C), 128.8 (4C), 128.2 (2C), 127.5 (4C); 126.7 (2C), 123.9 (1C), 123.6 (1C), 120.3 (1C), 119.8 (1C), 119.1 (1C), 115.4 (1C), 114.3 (2C), 83.8 (1C).
30. 13C NMR (acetone, ppm): δ = 149.7 (1C), 146.3 (1C), 145.5 (2C), 139.0 (1C), 137.9 (1C), 130.3 (1C), 128.2 (1C), 127.7 (1C), 129.6 (4C), 128.5 (2C), 127.6 (4C), 127.1 (2C), 120.7 (1C), 116.4 (1C), 113.6 (1C), 109.4 (2C), 82.1 (1C).
31. (5,8-Dimethyl-2,2-diphenyl-2H-chromen-6-yl)-(4-nitrophenyl)-amine 3c:. Shilova E.A., Moustrou C., and Samat A. Tetrahedron Lett. 46 (2005) 8857
32. 13C NMR (acetone, ppm): δ = 153.8 (1C), 145.9 (2C), 145.5 (1C), 139.6 (1C), 131.3 (1C), 130.1 (1C), 129.1 (4C), 128.4 (2C), 127.6 (4C), 127.5 (1C), 127.1 (1C), 126.8 (2C), 126.5 (1C), 122.6 (1C), 122.5 (1C), 114.5 (2C); 82.7 (1C), 20.9 (1C), 14.7 (1C).
33. 4), and purified by column chromatography with cyclohexane-acetone (90:10).
34. 2.