Novel Short-Step Synthesis of Functionalized γ-Phenyl-β-hydroxybutenoates and their Cyclization to 4-Hydroxycoumarins via the N-Hydroxybenzotriazole Methodology

Giorgos Athanasellis; Georgia Melagraki; Haralambos Chatzidakis; Antreas Afantitis; Anastasia Detsi; Olga Igglessi-Markopoulou; John Markopoulos

doi:10.1055/s-2004-829132

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Synthesis 2004(11): 1775-1782
DOI: 10.1055/s-2004-829132

PAPER

Novel Short-Step Synthesis of Functionalized γ-Phenyl-β-hydroxybutenoates and their Cyclization to 4-Hydroxycoumarins via the N-Hydroxybenzotriazole Methodology

Giorgos Athanasellis^a, Georgia Melagraki^a, Haralambos Chatzidakis^a, Antreas Afantitis^a, Anastasia Detsi^a, Olga Igglessi-Markopoulou*^a, John Markopoulos^b
^a National Technical University of Athens, School of Chemical Engineering, Laboratory of Organic Chemistry, Zografou Campus, Athens 15773, Greece
^b University of Athens, Department of Chemistry, Laboratory of Inorganic Chemistry, Panepistimiopolis, Zografou, Athens 15771, Greece
Fax: +3(210)7723072; e-Mail: ojmark@orfeas.chemeng.ntua.gr;

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Publication History

Received 27 November 2003
Publication Date:
01 July 2004 (online)

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Abstract

A novel method for the synthesis of functionalized 3-substituted 4-hydroxycoumarins is reported. C-Acylation compounds were derived from the reaction of the N-hydroxybenzotriazole ester of the functionalized acetyl salicylic acids and a variety of active methylene compounds and cyclized to the title compounds. The synthesis is simple and the compounds are produced in yields varying from 39 to 80%. The structure of the newly prepared C-acylation compounds was thoroughly studied through NMR spectroscopy for the first time in the literature.

Key words

coumarins - N-hydroxybenzotriazole - natural products - acylations - NMR spectroscopy - heterocycles

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