Triazolopyridines. Part 28. the ring-chain isomerization strategy: Triazolopyridine- and triazoloquinoline-pyridine based fluorescence ligands

Tetrahedron

Volumn 68, Issue 19, 2012, Pages 3701-3707

  Ballesteros Garrido, Rafael ^a   Delgado Pinar, Estefanía ^b   Abarca, Belén ^b   Ballesteros, Rafael ^b   Leroux, Frédéric R ^a   Colobert, Franoise ^a   Zaragozá, Ramón J ^b   García España, Enrique ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Cyanide sensing; Nitrite sensing; Quinolines; Triazolopyridines; Zinc(II) sensing

Indexed keywords

1 [6 ([1,2,3]TRIAZOLO[1,5 A]PYRIDIN 3 YL)PYRIDIN 2 YL] 1 [NAPHTHALEN 2 YL]ETHANOL; 2,6 BIS(4,5,6,7 TETRAHYDRO [1,2,3]TRIAZOLO[1,5 A]PYRIDIN YL)PYRIDINE; 2,6 BIS([1,2,3]TRIAZOLO[1,5 A]QUINOLIN 3 YL)PYRIDINE; 3 [6 ([1,2,3]TRIAZOLO[1,5 A]PYRIDIN 3 YL)PYRIDIN 2 YL] [1,2,3]TRIAZOLO[1,5 A]QUINOLINE; 6 ([1,2,3]TRIAZOLO[1,5 A]PYRIDIN 3 YL)PYRIDIN 2 YL ANTHRACEN 9 YL METHANOL; 6 ([1,2,3]TRIAZOLO[1,5 A]PYRIDIN 3 YL)PYRIDIN 2 YL QUINOLIN 2 YL METHANONE; COPPER COMPLEX; CYANIDE; LIGAND; NITRITE; PYRIDINE DERIVATIVE; QUINOLIN 2 YL 6 (QUINOLIN 2 YLCARBONYL)PYRIDIN 2 YL METHANONE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; BINDING AFFINITY; FLUORESCENCE; HYDROGENATION; ISOMERIZATION; METALLATION; PRIORITY JOURNAL; QUANTUM YIELD; RING CHAIN ISOMERIZATION; SENSOR; STOICHIOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 84859585698     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.029     Document Type: Article

References (47)

1. Triazolopyrines. Part 27. B. Abarca, R. Adam, and R. Ballesteros ARKIVOK iii 2010 319 327
2. H.C.V.D. Plas Ring Transformation of Heterocycles 1973 Academic London
3. R. Valters, and W. Fleitsch Ring-Chain Tautomerism 1985 Plenum New York
4. B. Abarca, I. Alkorta, R. Ballesteros, F. Blanco, M. Chadlaoui, J. Elguero, and F. Mojarrad Org. Biomol. Chem. 3 2005 3905 3910
5. R. Ballesteros-Garrido, F. Blanco, R. Ballesteros, F.R. Leroux, B. Abarca, F. Colobert, I. Alkorta, and J. Elguero Eur. J. Org. Chem. 2009 5765 5778
6. B. Abarca, R. Aucejo, R. Ballesteros, F. Blanco, and E. García-España Tetrahedron Lett. 47 2006 8101 8103
7. F. Colobert, R. Ballesteros-Garrido, F.R. Leroux, R. Ballesteros, and B. Abarca Tetrahedron Lett. 2007 6896 6899
8. B. Abarca, R. Ballesteros, R. Ballesteros-Garrido, F. Colobert, and F.R. Leroux Tetrahedron 63 2007 10479 10485
9. B. Abarca, R. Ballesteros, R. Ballesteros-Garrido, F. Colobert, and F.R. Leroux Tetrahedron 64 2008 3794 3801
10. B. Abarca, R. Ballesteros, and M. Chadlaoui Tetrahedron 60 2004 5785 5792
11. R. Ballesteros-Garrido, B. Abarca, R. Ballesteros, C. Ramírez de Arellano, F. Leroux, F. Colobert, and E. García-España New J. Chem. 33 2009 2102 2106
12. Z. Xu, J. Yoon, and D.R. Spring Chem. Soc. Rev. 39 2010 1996 2006
13. E.L. Que, D.W. Domaille, and C.J. Chang Chem. Rev. 108 2008 1517 1549
14. F. Wang, R. Peng, and Y. Sha Macromolecules 13 2008 922 930
15. X. Zhang, K.S. Lovejoy, A. Jasanoff, and S.J. Lippard Proc. Natl. Acad. Sci. U.S.A. 104 2007 10780 10785
16. D.W. Domaille, E.L. Que, and C.J. Chang Nat. Chem. Biol. 4 2008 168 175
17. K. Kikuchi, K. Komatsu, and T. Nagano Curr. Opin. Chem. Biol. 8 2004 182 191
18. W. Jiang, Q. Fu, H. Fan, and W. Wang Chem. Commun. 2008 259 269
19. Y. Shiraishi, C. Ichimura, and T. Hirai Tetrahedron Lett. 48 2007 7769 7773
20. J. Wang, Y. Xiao, Z. Zhang, X. Qian, Y. Yang, and Q. Xu J. Mater. Chem. 15 2005 2836 2839
21. A.E. Dennis, and R.C. Smith Chem. Commun. 2007 4641 4643
22. T. Hirano, K. Kikuchi, Y. Urano, T. Higuchi, and T. Nagano J. Am. Chem. Soc. 122 2000 12399 12400
23. B. Abarca, R. Ballesteros, and M. Elmasnaouy Tetrahedron 54 1998 15287 15292
24. J.H. Boyer, and N. Goebel J. Org. Chem. 25 1960 304 305
25. B. Abarca, R. Ballesteros, and M. Elmasnouy Tetrahedron 55 1999 12881 12884
26. B. Valeur, and I. Leray Coord. Chem. Rev. 205 2002 3 40
27. J.R. Lakowicz Principles of Fluorescence Spectroscopy second ed. 1999 Kluver Academic/Plenum New York
28. Y. Xiang, A. Tong, P. Jin, and Y. Ju Org. Lett. 8 2006 2863 2866
29. N.K. Singhal, B. Ramanujam, V. Mariappanadar, and C.P. Rao Org. Lett. 8 2006 3525 3528
30. M.-M. Yu, Z.-X. Li, L.-H. Wei, D.-H. Wei, and M.-S. Tang Org. Lett. 10 2008 5115 5118
31. HYPEQUAD P. Gans, A. Sabatini, and A. Vacca Talanta 43 1996 1739 1753
32. L. Shang, L. Jin, and S. Dong Chem. Commun. 2009 3077 3079
33. A. Touceda-Varela, E.I. Stevenson, J.A. Galve-Gasion, D.T.F. Dryden, and J.C. Mareque-Rivas Chem. Commun. 44 17 2008 1998 2000
34. K.-S. Lee, H.-J. Kim, G.-H. Kim, I. Shin, and J.-I. Hong Org. Lett. 10 2008 49 51
35. J. Ma, and P.K. Dasgupta Anal. Chim. Acta 673 2010 117 125
36. Z. Dai, and E.M. Boon J. Am. Chem. Soc. 132 2010 11496 11503
37. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M.B. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C. 02 2004 Gaussian Wallingford CT
38. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford University Press New York
39. T. Ziegler Chem. Rev. 91 1991 651 667
40. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
41. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
42. W.J. Hehre, L. Radom, P.V.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York
43. J. Tomasi, and M. Persico Chem. Rev. 94 1994 2027 2094
44. B.Y. Simkin Sheikhet, I Quantum Chemical and Statistical Theory of Solutions-A Computational Approach 1995 Ellis Horwood London
45. E. Cances, B. Mennunci, and J. Tomasi J. Chem. Phys. 107 1997 3032 3041
46. M. Cossi, V. Barone, R. Cammi, and J. Tomasi Chem. Phys. Lett. 255 1996 327 335
47. V. Barone, M. Cossi, and J. Tomasi J. Comput. Chem. 19 1998 404 417