New anthracenyl-substituted phosphonates: Synthesis and utility

Synthesis

Volumn , Issue 6, 2007, Pages 0893-0901

  Kumara Swamy, K C ^a   Srinivas, Venu ^a   Pavan Kumar, K V P ^a   Praveen Kumar, K ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Arenes; Cross coupling; Halogenation; Horner Wadsworth Emmons reaction; Phosphonates

Indexed keywords

ARENES; CROSS COUPLING; HORNER WADSWORTH EMMONS REACTION; PHOSPHONATES;

ALDEHYDES; AROMATIC COMPOUNDS; CHLORINATION; HALOGENATION; OLEFINS; SUBSTITUTION REACTIONS; X RAY DIFFRACTION ANALYSIS;

PHOSPHORUS COMPOUNDS;

10 (5,5 DIMETHYL 2 OXO 2LAMBDA 5 1,3,2 DIOXAPHOSPHINAN 2 YLMETHYLENE) 9,10 DIHYDROANTHRACEN 9 OL; 10 (5,5 DIMETHYL 2 OXO 2LAMBDA 5 1,3,2 DIOXAPHOSPHINAN 2 YLMETHYLENE)ANTHRACEN 9(10H) ONE; 2 (10 BROMOANTHRACEN 9 YLMETHYL) 5,5 DIMETHYL 2LAMBDA 5 1,3,2 DIOXAPHOSPHINAN 2 ONE; 2 (10 CHLOROANTHRACEN 9 YLMETHYL) 5,5 DIMETHYL 2LAMBDA 5 1,3,2 DIOXAPHOSPHINAN 2 ONE; 2 [ANTHRACEN 9 YL(CHLORO)METHYL] 5,5 DIMETHYL 2LAMBDA 5 1,3,2 DIOXAPHOSPHINAN 2 ONE; 4 [4 [2 (10 BROMOANTHRACEN 9 YL)VINYL]PHENYL] 2 METHYLBUT 3 YN 2 OL; 9 [2 (4 CHLOROPHENYL)VINYL]ANTHRACENE; 9 [2 (4 NITROPHENYL)VINYL]ANTHRACENE; 9 BROMO 10 [2 (4 BROMOPHENYL)VINYL]ANTHRACENE; 9 BROMO 10 [2 (4 METHOXYPHENYL)VINYL]ANTHRACENE; 9 BROMO 10 [2 (4 NITROPHENYL)VINYL]ANTHRACENE; 9 BROMO 10 [2 (4 OCT 1 YNYLPHENYL)VINYL]ANTHRACENE; 9 BROMO 10 [2 [4 PHENYLETHYNYL)PHENYL]VINYL]ANTHRACENE; 9 BROMO 10 STYRYLANTHRACENE; 9 OCT 1 YNYL 10 [2 (4 OCT 1 YNYLPHENYL)VINYL]ANTHRACENE; [2 (10 BROMOANTHRACEN 9 YL)VINYL]FERROCENE; ALKENE DERIVATIVE; ANTHRACEN 9 YL(5,5 DIMETHYL 2 OXO 2LAMBDA 5 1,3,2 DIOXAPHOSPHINAN 2 YL)METHANOL; ANTHRACENE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHLORINATION; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; HALOGENATION; HORNER WADSWORTH EMMONS REACTION; SYNTHESIS;

EID: 33947599993     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965947     Document Type: Article

References (42)

1. (a) Kim, Y.-H.; Shin, D.-C.; Kim, S.-H.; Ko, C.-H.; Yu, H.-S.; Chae, Y.-S.; Kwon, S.-K. Adv. Mater. 2001, 13, 1690.
2. (b) Ito, K.; Suzuki, T.; Sakamoto, Y.; Kubota, D.; Inoue, Y.; Sato, F.; Tokito, S. Angew. Chem. Int. Ed. 2003, 42, 1159.
3. (c) Ando, S.; Nishda, J.-i.; Fujiwara, E.; Tada, H.; Inoue, Y.; Tokito, S.; Yamashita, Y. Chem. Mater. 2005, 17, 1261.
4. (d) Sasaki, H.; Wakayama, Y.; Chikyow, T.; Barrena, E.; Dosch, H.; Kobayashi, K. Appl. Phys. Lett. 2006, 88, 081907.
5. (e) Cui, W.; Zhang, X.; Jiang, X.; Tian, H.; Yan, D.; Geng, Y.; Jing, X.; Wang, F. Org. Lett. 2006, 8, 785.
6. Photoswitches: (a) Schafer, C.; Mattay, J. Photochem. Photobiol. Sci. 2004, 3, 331.
7. Switch: (b) Callan, J. F.; De Silva, A. P.; McClenaghan, N. D. Chem. Commun. 2004, 2048.
8. OLED, DFT calculations: (c) Raghunath, P.; Reddy, M. A.; Gouri, C.; Bhanuprakash, K.; Jayathirtha Rao, V. J. Phys. Chem. A 2006, 110, 1152.
9. Bailey, D.; Williams, V. E. Chem. Commun. 2005, 2569.
10. (a) Becker, H. D. Chem. Rev. 1993, 93, 145.
11. (b) Laurent, H. B.; Castellan, A.; Desvergne, J.-P.; Lapouyade, R. Chem. Soc. Rev. 2000, 29, 43.
12. (c) Ihmels, H.; Leusser, D.; Pfeiffer, M.; Stalke, D. Tetrahedron 2000, 56, 6867.
13. (d) Jones, S.; Atherton, J. C. C. Tetrahedron: Asymmetry 2001, 12, 1117.
14. (e) Atherton, J. C. C.; Jones, S. Tetrahedron Lett. 2002, 43, 9097.
15. Diels-Alder reaction: (f) Bawa, R. A.; Jones, S. Tetrahedron 2004, 60, 2765.
16. (g) Atherton, J. C. C.; Jones, S. Tetrahedron 2003, 59, 9039.
17. (h) Horiguchi, M.; Ito, Y. J. Org. Chem. 2006, 71, 3608.
18. Iwamoto, E.; Hirai, K.; Tomioka, H. J. Am. Chem. Soc. 2003, 125, 14664.
19. DNA cleavage, anthracene derivatives: (a) Tan, W. B.; Bhambhani, A.; Duff, M. R.; Rodger, A.; Kumar, C. V. Photochem. Photobiol. 2006, 82, 20.
20. (b) Ghosh, T.; Maiya, B. G.; Samanta, A.; Shukla, A. D.; Jose, D. A.; Kumar, D. K.; Das, A. J. Biol. Inorg. Chem. 2005, 10, 496.
21. (c) Marques, F.; Paulo, A.; Campello, M. P.; Lacerda, S.; Vitor, R. F.; Gano, L.; Delgado, R.; Santos, I. Radiat. Prot. Dosim. 2005, 116, 601.
22. Cakmak, O.; Erenler, R.; Tutar, A.; Celik, N. J. Org. Chem. 2006, 71, 1795.
23. Reports in which such anthracenyl compounds are utilized for two photon cross-sections: (a) Yang, W. J.; Kim, C. H.; Jeong, M.-Y.; Lee, S. K.; Piao, M. J.; Jeon, S.-J.; Cho, B. R. Chem. Mater. 2004, 16, 2783.
24. Phosphonate: (b) Lee, S. K.; Yang, W. J.; Choi, J. J.; Kim, C. H.; Jeon, S.-J.; Cho, B. R. Org. Lett. 2005, 7, 323.
25. (a) Kumaraswamy, S.; Selvi, R. S.; Kumara Swamy, K. C. Synthesis 1997, 207.
26. (b) Praveen Kumar, K.; Muthiah, C.; Kumaraswamy, S.; Kumara Swamy, K. C. Tetrahedron Lett. 2001, 42, 3219.
27. (c) Muthiah, C.; Praveen Kumar, K.; Aruna Mani, C.; Kumara Swamy, K. C. J. Org. Chem. 2000, 65, 3733.
28. Iorga, B.; Eymery, F.; Savignac, P. Tetrahedron 1999, 55, 2671.
29. Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron 2004, 60, 203.
30. In normal Horner-Wadsworth-Emmons reactions, hydrogen is eliminated by the base to produce the carbanion, which then reacts with the aldehyde.
31. Said, M. A.; Kumara Swamy, K. C.; Chandra Mohan, K.; Venkata Lakshmi, N. Tetrahedron 1994, 50, 6989.
32. Shokol, V. A.; Kozhushko, B. N. Russ. Chem. Rev. 1985, 54, 98.
33. Duan, S.; Turk, J.; Speigle, J.; Corbin, J.; Masnovi, J.; Baker, R. J. J. Org. Chem. 2000, 65, 3005.
34. 1H NMR]. In the normal reaction, the C-Cl moiety is retained: see: (a) Kumaraswamy, S.; Kumara Swamy, K. C. Tetrahedron Lett. 1997, 38, 2183.
35. (b) Muthiah, C.; Praveen Kumar, K.; Kumaraswamy, S.; Kumara Swamy, K. C. Tetrahedron 1998, 54, 14315.
36. 3): product a: δ = 6.75 (d, J = 16.0 Hz, 1 H, olefinic-H), 6.84 (dd, J = 10.8, 16.0 Hz, 1 H, olefmic-H), 7.25-7.58 (m, 11 H, phenyl-H, anthryl-H), 8.03, 8.37 (d with virtual coupling, 4 H, anthryl-H), 8.42 (s, 1 H, anthryl-H). Product b: δ = 6.74-6.82 (m, 2 H, olefinic-H), 7.25-7.66 (m, 11 H, phenyl-H, anthryl-H, olefinic-H), 8.38 (d, J = 8.8 Hz, 2 H, anthryl-H), 8.58 (d, J = 8.8 Hz, 2 H, anthryl-H)].
37. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
38. (b) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
39. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon: Oxford, 1986.
40. A program for crystal structure solution and refinement: (a) Sheldrick, G. M. SHELX-97; University of Göttingen: Germany, 1997.
41. (b) Sheldrick, G. M. SADABS, Siemens Area Detector Absorption Correction; University of Gottingen: Germany, 1996.
42. (c) Sheldrick, G. M. SHELXTLNT Crystal Structure Analysis Package, Version 5.10; Bruker Analytical X-ray System: WI, 1999.