Using molecular iodine in direct oxidative condensation of aldoses with diamines: an improved synthesis of aldo-benzimidazoles and aldo-naphthimidazoles for carbohydrate analysis

The Journal of Organic Chemistry
Chunchi LinJim-Min Fang

Abstract

A practical method has been developed for conversion of unprotected and unmodified aldoses to aldo-benzimidazoles and aldo-naphthimidazoles. Using iodine as an oxidant or promoter in acetic acid solution, a series of mono-, di-, and trialdoses, including those containing carboxyl and acetamido groups, undergo an oxidative condensation reaction with o-phenylenediamine or 2,3-naphthalenediamine at room temperature to give the aldo-benzimidazole and aldo-naphthimidazole products in high yields. No cleavage of the glycosidic bond occurs under such mild reaction conditions. The composition analysis of saccharides is realized by the HPLC analysis of the fluorescent naphthimidazole derivatives.

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Citations

Jun 21, 2011·Journal of Natural Products·Tzong-Huei LeeYu-Min Ju
Aug 10, 2012·Organic Letters·Gary A Molander, Kehinde Ajayi
Mar 12, 2011·Journal of Mass Spectrometry : JMS·Yu-Ling ChangYuan Chuan Lee
Jan 5, 2017·Chemical & Pharmaceutical Bulletin·Eito YoshiokaHideto Miyabe
Jun 19, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chien-Yuan KuoWen-Bin Yang
May 2, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wei-Ting HungWen-Bin Yang
Mar 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chunchi LinWen-Bin Yang
Jan 19, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chunchi LinWen-Bin Yang
Dec 5, 2009·Rapid Communications in Mass Spectrometry : RCM·Chunchi LinWen-Bin Yang
Apr 11, 2012·Chemistry : a European Journal·Prakash T ParvatkarSantosh G Tilve
Dec 13, 2019·Organic Letters·Jiao LiMaoluo Gan

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