Quaternization of N‐Heterocycles with Propylene Oxide and Epichlorohydrin

References

• Cosa , G. , Focsaneanu , K.‐S. , McLean , J. , McNamee , J. and Scaiano , J. 2001 . Photophysical properties of fluorescent DNA‐dyes bound to single‐ and double‐stranded DNA in aqueous buffered solution . Photochem. Photobiol. , 73 : 585 – 599 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Rye , H. , Yue , S. , Wemmer , D. , Quesada , M. , Haugland , R. , Mathies , R. and Glazer , A. 1992 . Stable fluorescent complexes of double‐stranded DNA with bis‐intercalating asymmetric cyanine dyes. Properties and applications . Nucl. Acids Res. , 20 : 2803 – 2812 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Prodhomme , S. , Demaret , J. , Vinogradov , S. , Asseline , U. , Morin‐Allory , L. and Vigny , P. 1999 . J. Photochem. Photobiol. B: Biol. , 53 : 60 – 69 . [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Warner , I. M. , Soper , S. A. and McGown , L. B. 1996 . Molecular fluorescence, phosphorescence, and chemiluminescence spectrometry . Anal. Chem. , 68 : 73R – 91R . [CROSSREF]
   Web of Science ®Google Scholar
• Haugland , R. 2002 . Handbook of Fluorescent Probes and Research Chemicals , 9th Ed. , Molecular Probes Eugene, OR
   Google Scholar
• Deligeorgiev , T. , Timcheva , I. , Maximova , V. , Gadjev , N. and Drexhage , K.‐H. 2002 . Fluorescence characteristics of variously charged asymmetric monomethine cyanine dyes in the presence of nucleic acids . J. Fluoresc. , 12 ( 2 ) : 225 – 229 . [CROSSREF]
   Web of Science ®Google Scholar
• Deligeorgiev , T. , Gadjev , N. , Timcheva , I. , Maximova , V. , Katerinopoulos , H. and Foukaraki , E. 2000 . Synthesis of homodimeric monomethine cyanine dyes as noncovalent nucleic acid labels and their absorption and fluorescence spectral characteristics . Dyes and Pigments , 44 : 131 – 136 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Gadjev , N. , Deligeorgiev , T. and Kim , S. 1999 . Preparation of monomethine cyanine dyes as noncovalent labels for nucleic acids . Dyes and Pigments , 40 : 181 – 186 . [CROSSREF]
   Web of Science ®Google Scholar
• Deligeorgiev , T. and Gadjev , N. 1995 . Preparation of intercalating dye thiazole orange and derivatives . Dyes and Pigments , 29 ( 4 ) : 315 – 322 . [CROSSREF]
   Web of Science ®Google Scholar
• Hamer , F. 1974 . “ The chemistry of heterocyclic compounds ” . In The Cyanine Dyes and Related Compounds Edited by: Weissberger , A. Vol. 18 , New York : Interscience Publishers .
   Google Scholar
• Sturmer , D. and Heseltine , D. 1977 . “ The theory of the photographic process ” . In Sensitizing and Desensitizing Dyes Edited by: James , T. 194 – 234 . New York : Macmillan Co. .
   Google Scholar
• Zollinger , H. 1991 . “ Synthesis, properties and applications of organic dyes and pigments ” . In Color Chemistry 65 – 69 . Weinheim : VCH Publishers Inc. .
   Google Scholar
• Kleinpeter , E. , Borsdorf , R. and Dietz , F. 1973 . Zur Reactivität der 2‐Methylcyclammoniumsalce . J. Prakt. Chem. , 315 : 600 – 610 .
   Google Scholar
• Jaroszewska , J. , Wawer , I. and Oszczapowicz , J. 1984 . Carbon‐13 and proton spectral studies of N‐alkylmethylquinolinium salts . J. Org. Magn. Reson. , 22 : 323 – 327 .
   Web of Science ®Google Scholar
• Chupakhin , O. N. , Balakin , V. M. and Kokoshko , Z. U. 1968 . Quaternary salts of some N‐containing heterocycles. I Synthensis of derivatives of 1,3‐dichloro‐2‐propanol and their UV spectra (in Russian). Khim . Geterocycl. Soedin. , 5 : 859
   Google Scholar
• Pardal , A. , Ramos , S. , Santos , P. , Reis , L. and Almeida , P. 2002 . Synthesis and spectroscopic characterization of N‐alkyl quaternary ammonium salts typical precursors of cyanines . Molecules , 7 : 320 – 330 .
   Web of Science ®Google Scholar
• King , L. , Berst , N. and Hayes , F. 1949 . Reactions of 1,2‐epoxides with salts of organic bases. I. Styrene oxide . J. Am. Chem. Soc. , 71 : 3498 – 3500 .
   Web of Science ®Google Scholar
• Hayes , F. , King , L. and Peterson , D. 1956 . Reactions of 1,2‐epoxides with salts of organic bases. II. Cyclohexene oxide . J. Am. Chem. Soc. , 78 : 2527 – 2528 .
   Web of Science ®Google Scholar
• Garkusha‐Boshko , V. and Shvajka , O. 1990 . Reactions of pyridinium compounds with epichlorohydrin . Khim. Geterocycl. Soedin. , : 507 – 510 .
   Google Scholar
• Meisel , K. , Walz , K. , Renner , G. F. , Schulze , H. , Gerdes , C. , Gassen , K. R. , Ditzer , R. and Klein , L. Process for the Preparation of Beta‐hydroxyalkylpycolinium Salts . EP 776888 . June 04, 1997 . CA:127: 81358p, 1997
   Google Scholar
• Rao , A. , Paknikar , S. and Kirfane , J. 1983 . Recent advances in the preparation and synthetic applications of oxiranes . Tetrahedron , 39 ( 14 ) : 2323 – 2361 . [CROSSREF]
   Web of Science ®Google Scholar
• Kakiuchi , H. and Iijima , T. 1980 . The ring‐opening reactions of propylene oxide with chloroacetic acids . Tetrahedron , 36 : 1011 – 1016 . [CROSSREF]
   Web of Science ®Google Scholar
• Deligeorgiev , T. and Simov , D. 1998 . Preparation of cationic azo dyes derived from 2‐amino‐6‐(2‐chloroethoxy)benzothiazole and 2‐amino‐4‐(2‐hydroxyethoxy)benzothiazole . Dyes and Pigments , 38 ( 1–3 ) : 115 – 125 . [CROSSREF]
   Web of Science ®Google Scholar