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Paper | Regular issue | Vol 65, No. 5, 2005, pp.1051-1061
Published online, 1st March, 2005
DOI: 10.3987/COM-05-10332
Functional 1,3-Benzodioxoles Making a Fluorescent Response to Local Transformation in Chemo-reactive Pendant Groups

Masaya Suzuki, Yoshihiro Nishida,* Yuya Ohguro, and Kazukiyo Kobayashi

*Department of Molecular Design & Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


From bi-functional methyl 5-nitro-1,3-benzodioxole-4-carboxylates designed as artificial β-amino acid homologues, a series of chemo-functional 5-amide derivatives (acrylamide, maleimide, 4-azidobenzamide and 4-vinylbenzamide) were prepared. These functional compounds were non-fluorescent while they all gave fluorescent products in the corresponding thiol coupling, photo-activated transformation, hydrogenation, and polymerization reations.