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Synlett 2006(8): 1225-1229  
DOI: 10.1055/s-2006-941564
LETTER
© Georg Thieme Verlag Stuttgart · New York

Application of a Regioselective Mannich Reaction on Naringenin and its Use in Fluorescent Labeling

Lei Chen, Tai-Shan Hu, Jing Zhu, Houming Wu, Zhu-Jun Yao*
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: yaoz@mail.sioc.ac.cn;
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Publication History

Received 2 December 2005
Publication Date:
05 May 2006 (online)

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Abstract

A novel strategy for site-specific fluorescent labeling on naringenin (1) was established by a new direct Mannich reaction in combination with a Huisgen [3+2]-cycloaddition reaction. High ­regioselectivity was observed for direct Mannich reactions on ­naringenin and several other flavonones using a variety of amines and aldehydes.

Key words

naringenin - Mannich reaction - Huisgen cycloaddition - regioselectivity - fluorescent labeling

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  • 20 General Procedure: To a solution of naringenin (1 mmol) and paraformaldehyde or acetaldehyde (1.5 mmol) in EtOH (4 mL) was added the secondary amine (1.5 mmol) at r.t. The mixture was then heated to 40-65 °C, depending on the secondary amine (see Table 1), and the reaction was monitored by TLC. After the reactants were consumed, EtOAc (30 mL) and diluted HCl (30 mL, pH 3) were added to the mixture. Then the pH of the aqueous phase was adjusted to 7. The aqueous phase was extracted with EtOAc (3 × 15 mL). The combined extracts were dried over anhyd Na2SO4. The crude product was purified by silica gel chromatography