Functionalization of aminocrown ethers with [2H]-chromene units by Buchwald-Hartwig C-N coupling for constructing of photoswitchable molecular devices

Tetrahedron Letters

Volumn 46, Issue 51, 2005, Pages 8857-8859

  Shilova, Ekaterina A ^a,b   Moustrou, Corinne ^a   Samat, André ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

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

Author keywords

2H 1 Benzopyrane; 2H Chromene; Buchwald Hartwig C N coupling; Diaminodibenzocrown ether; Naphtho 2,1 b pyrane; Photoswitchable devices

Indexed keywords

2H [1]BENZOPYRANE; 3H NAPHTHO[2,1 B]PYRANE; CHROMENE DERIVATIVE; CROWN ETHER DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; DEVICE; PHOTOREACTIVITY;

EID: 27944484958     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.069     Document Type: Article

References (26)

1. Nobel Lectures, Chemistry, 1981-1990, Pedersen, C. The Discovery of Crown Ethers. December 8, 1987; World Scientific Publishing: Singapore; 1992.
2. F. Vögtle Comprehensive Supramolecular Chemistry Vol. 2 1996 Pergamon Oxford
3. J.-M. Lehn Supramolecular Chemistry: Concepts and Perspective 1995 Wiley Weinheim
4. F.M. Raymo, and S. Giordani J. Am. Chem. Soc. 123 2001 4651 4652
5. F.M. Raymo, and S. Giordani Org. Lett. 3 2001 1833 1836
6. F.M. Raymo, and S. Giordani Org. Lett. 3 2001 3475 3478
7. F.M. Raymo, R.J. Alvarado, S. Giordani, and M.A. Cejas J. Am. Chem. Soc. 125 2003 2361 2364
8. S. Giordani, and F.M. Raymo Org. Lett. 5 2003 3559 3562
9. X.-F. Guo, D.-Q. Zhang, Y.-C. Zhou, and D.-B. Zhu Chem. Phys. Lett. 375 2003 484 489
10. X.-F. Guo, D.-Q. Zhang, Y.-C. Zhou, and D.-B. Zhu J. Org. Chem. 68 2003 5681 5687
11. A. Grofcsik, P. Baranyai, I. Bitter, A. Grün, E. Köszegi, M. Kubinyi, K. Pál, and T.J. Vidóczy Mol. Struct. 614 2002 69 73
12. J.H.R. Tucker, H. Bouas-Laurent, P. Marsau, S.W. Riley, and J.-P. Desvergne Chem. Commun. 1997
13. K. Kimura, T. Teranishi, M. Yokoyama, S. Yajima, S. Miyake, H. Sakamoto, and M. Tanaka J. Chem. Soc., Perkin Trans. 2 1999 199 204
14. K. Kimura, H. Sakamoto, S. Kado, R. Arakawa, and M. Yokoyama Analyst 125 2000 1091 1095
15. S. Jockusch, J.N. Turro, and R. Blackburn J. Phys. Chem. A 106 2002 9236 9241
16. N.M.F.S.A. Serqueira, A.M.F. Oliveira-Campos, P.J. Coelho, L.H.M. Carvalho, A. Samat, and R. Gugliemetti Helv. Chim. Acta 85 2002 442 450
17. J.P. Wolfe, S. Wagaw, and S.L. Buchwald J. Am. Chem. Soc. 118 1996 7215 7216
18. J.P. Wolfe, and S.L. Buchwald Tetrahedron Lett. 38 1997 6359 6362
19. J.P. Wolfe, S. Wagaw, J.-F. Marcoux, and S.L. Buchwald Acc. Chem. Res. 31 1998 805 818
20. B.H. Yang, and S.L. Buchwald J. Organomet. Chem. 576 1999 125 146
21. J.P. Wolf, and S.L. Buchwald J. Org. Chem. 65 2000 1144 1157
22. Bougdid, L. Ph.D. Thesis, Université de la Mé diterranée; 2005.
23. 13C NMR (acetone, ppm): δ = 154.7 (1C), 150.1 (1C), 146.5 (2C), 139.0 (1C), 131.9 (1C), 130.3 (1C), 130.2 (1C), 130.0 (1C), 129.24 (4C), 128.48 (2C), 127.6 (4C), 127.0 (2C); 125.1 (1C), 122.2 (1C), 121.8 (1C), 113.0 (2C), 82.6 (1C), 16.0 (1C), 13.4 (1C).
24. M. Frigoli, C. Moustrou, A. Samat, and R. Gugliemetti Helv. Chim. Acta 83 2000 3043 3051
25. 13C NMR (acetonitrile, ppm): δ = 148.6 (2C), 148.2 (2C), 147.1 (2C), 146.1 (4C), 142.2 (2C), 135.8 (2C), 129.8 (2C), 128.9 (8C), 128.1 (4C), 127.0 (8C), 125.7 (2C), 124.2 (2C); 122.63 (2C), 121.6 (2C), 112.5 (2C), 112.0 (2C), 107.2 (2C), 101.8 (2C), 81.5 (2C), 69.6 (4C), 67.64 (4C).
26. 13C NMR (acetonitrile, ppm): δ = 153.2 (2C), 151.5 (2C), 147.6 (2C), 147.3 (2C), 145.5 (2C), 143.7 (4C), 133.1 (2C), 130.8 (4C), 130.5 (4C), 129.3 (8C), 128.8 (2C), 128.7 (4C), 126.4 (2C), 125.2 (2C); 124.47 (2C), 124.0 (2C), 120.3 (2C), 116.6 (2C), 114.2 (2C), 112.6 (2C), 111.9 (2C), 106.5 (2C), 83.8 (2C), 71.0 (4C), 67.0 (4C).