One-pot synthesis of N, N, N, N-tetraethyl-9H-xanthene-3,6-diamine and its conversion to pyronine B

Dyes and Pigments

Volumn 96, Issue 1, 2013, Pages 59-62

  Han, Shulei ^a   Chen, Yi ^a  

^a TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

Fluorescent dye; N, N, N, N tetraethyl 9H xanthene 3,6 diamine; One pot; Photo conversion; Pyronine B; Synthesis

Indexed keywords

COLOR CHANGES; FLUORESCENT DYES; ONE POT; ONE-POT REACTION; ONE-POT SYNTHESIS; PHOTO-CONVERSION; PROTONATED; PYRIDINIUM; SIMPLE APPROACH;

FLUORESCENCE;

SYNTHESIS (CHEMICAL);

EID: 84865403066     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.03.034     Document Type: Article

References (44)

1. L. Plistil, T. Solomek, J. Wirz, D. Heger, and P. Klan Photochemistry of 2-alkoxymethyl-5-methylphenacyl chloride and benzoate J Org Chem 71 2006 8050 8058
2. H.E. Zimmerman, and S. Shorunov Heterocyclic photochemistry in contrast with carbon behavior. Regioselective photochemical rearrangement of an azacyclohexadienone: mechanistic and exploratory organic photochemistry(1) J Org Chem 74 2009 5411 5416
3. P. Rudolf, J. Buback, J. Aulbach, P. Nuernberger, and T. Brixner Ultrafast multisequential photochemistry of 5-diazo meldrum's acid J Am Chem Soc 132 2010 15213 15222
4. S.J. Sarma, and P.B. Jones Photochemistry of 1, n-dibenzyloxy-9,10- anthraquinones J Org Chem 75 2010 3806 3813
5. M. Freccero, M. Fagnoni, and A. Albini Homolytic vs heterolytic paths in the photochemistry of haloanilines J Am Chem Soc 125 2003 13182 13190
6. A.D. Ostrowshi, S.J. Deakin, B. Azhar, T.W. Miller, N. Franco, and M.M. Cherney Nitric oxide photogeneration from trans-cr(cyclam)(ono)2+ in a reducing environment. Activation of soluble guanylyl cyclase and arterial vasorelaxation J Med Chem 53 2010 715 722
7. S. Dong, H. Hwang, X. Shi, L. Holloway, and H. Yu Uva-induced dna single-strand cleavage by 1-hydroxypyrene and formation of covalent adducts between dna and 1-hydroxypyrene Chem Res in Toxicol 13 2000 585 593
8. K.H. Kim, X.J. Fan, and P.E. Nielsen Efficient sequence-directed psoralen targeting using pseudocomplementary peptide nucleic acids Bioconjug Chem 18 2007 567 572
9. Y.A. Shieh, S.J. Yang, M.F. Wei, and M.J. Shieh Aptamer-based tumor-targeted drug delivery for photodynamic therapy ACS Nano 4 2010 1433 1442
10. J. Morgan, J.D. Jackson, X. Zheng, S.K. Pandey, and R.K. Pandey Substrate affinity of photosensitizers derived from chlorophyll-a: the abcg2 transporter affects the phototoxic response of side population stem cell-like cancer cells to photodynamic therapy Mol Pharmaceutics 7 2010 1789 1804
11. J. Klanova, P. Klan, J. Nosek, and I. Holoubek Environmental ice photochemistry: monochlorophenols Environ Sci Technol 37 2003 1568 1574
12. C. Lee, W. Choi, and J. Yoon UV photolytic mechanism of n-nitrosodimethylamine in water: roles of dissolved oxygen and solution PH Environ Sci Technol 39 2005 9702 9709
13. 2 nanotube array electrode under visible light irradiation Environ Sci Technol 44 2010 5098 5103
14. A.C. Herath, R.M.G. Rajapakse, A. Wicramasinghe, and V. Karunaratne Photodegradation of triphenylamino methane (magenta) by photosensitizer in oxygenated solutions Environ Sci Technol 43 2009 176 180
15. D.J. Kang, and B.S. Bae Photo-imageable sol-gel hybrid materials for simple fabrication of micro-optical elements Acc Chem Res 40 2007 903 912
16. M. Faustini, L. Nicole, C. Boissire, P. Innocenzi, C. Sanchez, and D. Grosso Hydrophobic, antireflective, self-cleaning, and antifogging sol-gel coatings: an example of multifunctional nanostructured materials for photovoltaic cells Chem Mater 22 2010 4406 4413
17. D. Kessler, F.D. Jochum, J. Choi, K. Char, and P. Theato Reactive surface coatings based on polysilsesquioxanes: universal method toward light-responsive surfaces ACS Appl Mater Interfaces 3 2011 124 128
18. M.K.R. Fisher, I. Lopez-Duarte, M.M. Wienk, M.V. Martinez-Diaz, R.A.J. Janssen, and P. Bauerle Functionalized dendritic oligothiophenes: ruthenium phthalocyanine complexes and their application in bulk heterojunction solar cells J Am Chem Soc 131 2009 8669 8676
19. E. Hwang, I.I. Smolyaninov, and C.C. Davis Surface plasmon polariton enhanced fluorescence from quantum dots on nanostructured metal surfaces Nano Lett 10 2010 813 820
20. M. Kawamoto, T. Sassa, and T. Wada Photoinduced control over the self-organized orientation of amorphous molecular materials using polarized light J Phys Chem B 114 2010 1227 1232
21. N. Kawatsuki, R. Tsutsumi, H. Takatsuka, and T. Sakai Influence of alkylene spacer length on thermal enhancement of photoinduced optical anisotropy in photo-cross-linkable liquid crystalline polymeric films and their composites with non-liquid-crystalline monomers Macromolecules 40 2007 6355 6360
22. T. Mitamura, K. Iwata, and A. Ogawa Photoinduced intramolecular cyclization of o-ethenylaryl isocyanides with organic disulfides mediated by diphenyl ditelluride J Org Chem 76 2011 3880 3887
23. H. Yu, T. Iyoda, and T. Ikeda Photoinduced alignment of nanocylinders by supramolecular cooperative motions J Am Chem Soc 128 2006 11010 11011
24. D. Han, X. Tong, Y. Zhao, T. Galstian, and Y. Zhao Cyclic azobenzene-containing side-chain liquid crystalline polymers: synthesis and topological effect on mesophase transition, order, and photoinduced birefringence Macromolecules 43 2010 3664 3671
25. A. Arnone, L. Merlini, and G. Nasini Santalin pigments: on the structure of santalin a original research article Tetrahedron Lett 13 1972 3503 3506
26. B. Ravindranath, and T.R. Seshadri Structural studies on santalin permethyl ether Phytochemistry 12 1973 p. 2781-1
27. N. Kumar, and T.R. Sechadri Chemical components of Pterocarpus santalinus sapwood Curr Sci 43 1974 611 612
28. A. Arnone, L. Camarda, L. Merlini, G. Nasini, and D.A.H. Taylor Colouring matters of the west African red woods Pterocarpus osun and P. soyauxii. Structures of santarubins A and B J Chem Soc Perkin Trans I 1977 2116 2118
29. J. Kinjo, H. Uemura, T. Nahara, M. Yamashita, N. Marubayashi, and K. Yoshihira Novel yellow pigment from Pterocarpus santalinus: biogenetic hypothesis for santalin analogs Tetrahedron Lett 36 1995 5599 5602
30. 4th ed. M.E. Wolff Burger's medicinal chemistry Part III 1981 John Wiley & Sons, Inc New York 393 407
31. D. Lednicer, and L.A. Metscher Organic chemistry of drug synthesis 1977 John Wiley & Sons, Inc New York p. 859-1067
32. N. Sato, M. Jitsuoka, T. Shibata, T. Hirohashi, K. Nomoshita, and M. Moriya (9S)-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-2,3, 4,9-tetrahydro-1H-xanthen-1-one, a selective and orally active neuropeptide Y Y5 receptor antagonist J Med Chem 51 2008 4765 4770
33. N. Sato, T. Takahashi, T. Shiabata, Y. Haga, A. Sakuraba, and M. Hirose Design and synthesis of the potent, orally available, brain-penetrable arylpyrazole class of neuropeptide Y5 receptor antagonists J Med Chem 46 2003 666 669
34. R. Pellicciari, G. Costantino, M. Marinozzi, A. Macchiarulo, L. Amori, and P.J. Flor Design, synthesis and preliminary evaluation of novel 3′-substituted carboxycyclopropylglycines as antagonists at group 2 metabotropic glutamate receptors Bioorg Med Chem Lett 11 2001 3179 3182
35. V.B. Birman, A. Chopra, and C.A. Ogle A novel approach to tricyclic pharmaceuticals via directed dilithiation of diaryl compounds Tetrahedron Lett 37 1996 5073 5076
36. M. Kamel, and H. Shoeb Dibenzoxanthylium salts - iv: studies on 1,2,5,6-dibenzo- and 2,3,5,6-dibenzo-xanthylium compounds Tetrahedron 20 1964 491 495
37. A.R. Katritzky, P. Czerney, and J.R. Level Benzotriazole-mediated conversions of para-h-substituted pyrylium, benzo[b]pyrylium, and xanthylium salts into para-position functionalized derivatives (an indirect electrophilic substitution of electron-deficient heteroaromatics) J Org Chem 62 1997 8198 8200
38. Menchen SM, Benson SC, Lam JYL, Zhen W, Sun D, Rosenblum BB, et al. Process for producing polymaleimide. U.S. Patent, US 6583168; 2003.
39. Reynolds GA, Tuccio SA, Peterson OG, Specht DP. Ger. Offen. Germany Patent; DE2109040; 1971.
40. M. Tsotsalas, M. Busby, E. Gianolio, S. Aime, and L. De Cola Functionalized nanocontainers as dual magnetic and optical probes for molecular imaging applications Chem Mater 20 2008 5888 5893
41. E.K. Paleologos, M.A. Koupparis, M.I. Karayannis, and P.G. Veltsistas Nonaqueous catalytic fluorometric trace determination of vanadium based on the pyronine b-hydrogen peroxide reaction and flow injection after cloud point extraction Anal Chem 73 2001 4428 4433
42. E. Vuorimaa, and H. Lemmetyinen Intralayer and interlayer energy transfer between octadecyl substituted pyronine and crystal violet incorporated in langmuir-blodgett films: a time-resolved study Langmuir 13 1997 3009 3015
43. B. Reija, W. Al-Soufi, M. Novo, and J.V. Tato Specific interactions in the inclusion complexes of pyronines Y and B with β-cyclodextrin J Phys Chem B 109 2005 1364 1370
44. Clunas S, Strory JMD, Rickard JE, Horsley D, Harrington CR, Wischik CM. 3,6-disubstituted xanthylium salts. Patent WO2010/067078; 2010.