DOI: 10.1039/A605012C
(Paper)
Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1051-1058
Synthesis of functionalised fluorescent dyes and their coupling to amines and amino acids
(Note: The full text of this document is currently only available in the PDF Version )
Mark S. J. Briggs, Ian Bruce, James N. Miller, Christopher J. Moody, Adrian C. Simmonds and Elizabeth Swann
Abstract
A series of novel functionalised benzophenoxazinones, analogues of Nile Red, is prepared and their fluorescence properties evaluated. The ring system is prepared by reaction of 5-diethylamino-2-nitrosophenol with 1,6-dihydroxynaphthalene followed by alkylation of the 2-hydroxy group with 6-bromohexanoic acid derivatives. Subsequent ester cleavage under a variety of conditions gives the acid 6. Replacement of the 9-diethylamino group with the N-ethyl-(3-sulfonylpropyl)amino group is carried out to increase water solubility and the resulting dye 14 has similar fluorescence properties. The acid 6 is coupled to a range of amino compounds.
References
- For overviews see: (a) Infra-red Absorbing Dyes, ed. M. Matsuoka, Plenum Press, New York, 1990 Search PubMed; (b) G. Patonay and M. D. Antoine, Anal. Chem., 1991, 63, 321A CAS; (c) R. M. Christie, Rev. Prog. Coloration, 1993, 23, 1 Search PubMed; (d) R. B. Mujumdar, L. A. Ernst, S. R. Mujumdar, C. J. Lewis and A. S. Waggoner, Bioconjugate Chem., 1993, 4, 105 CrossRef CAS.
- For reviews on phenoxazines, see; Rodd's Chemistry of Carbon Compounds, 2nd edn., ed. S. Coffey, vol. IVH, p. 471 Search PubMed; R. Raue, ‘Azine Dyes’, in Ullmann's Encyclopedia of Industrial Chemistry, 5th edn., vol. A3, p. 213 Search PubMed; M. Sainsbury, Comprehensive Heterocyclic Chemistry, eds. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 3, p. 995 Search PubMed.
- N. N. Alekseev, A. Ya. Gorelenko and N. N. Vasil'ev, Otkrytiya, Izobret., Prom. Obraztsy, Tovarnye Znaki, 1984, 31, 66 Search PubMed; Chem. Abstr., 1984, 101, 230 551 Search PubMed.
- H. Heaney, Encyclopedia of Reagents for Organic Synthesis, John Wiley, 1995, vol.1, p. 661 Search PubMed.
- E. D. Laganis and B. L. Chenard, Tetrahedron Lett., 1984, 25, 5831 CrossRef CAS.
- K. Kobayashi, C. L. Gajurel, K. Umemoto and Y. Mazaki, Bull. Chem. Soc. Jpn., 1992, 65, 2168 CAS.
- R. W. Dugger and C. H. Heathcock, Synth. Commun., 1980, 10, 509 CAS.
- B. Mauzé and L. Miginiac, Synth. Commun., 1990, 20, 2251 CAS.
- N. Martin, J. A. Navarro, C. Seoane, A. Albert, F. H. Cano, J. Y. Becker, V. Khodorkovsky, E. Harlev and M. Hanack, J. Org. Chem., 1992, 57, 5726 CrossRef CAS.