Reactivity of 4-Vinyl-2H-1-benzopyran-2-ones in Diels-Alder Cycloaddition Reactions: Access to Coumarin-Based Polycycles with Cdc25 Phosphatase-Inhibiting Activity - Université de Lorraine Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2013

Reactivity of 4-Vinyl-2H-1-benzopyran-2-ones in Diels-Alder Cycloaddition Reactions: Access to Coumarin-Based Polycycles with Cdc25 Phosphatase-Inhibiting Activity

Abstract

The reactivity of 4-(1-butoxyvinyl)-2H-chromen-2-one (1) and (E)-4-(2-butoxyvinyl)-2H-chromen-2-one (2) as diene in thermal DielsAlder cycloaddition reactions with several electron-poor dienophiles is reported. Among several dienophiles used in this study 1,4-benzoquinone afforded cycloadducts 11-butoxy-1H-naphtho[1,2-c]chromene-1,4,5-trione (3e) and 1H-naphtho[1,2-c]chromene-1,4,5-trione (4g) that showed Cdc25 phosphatase-inhibition activity at low micromolar values, with both compounds more effective against Cdc25 A and Cdc25 C isoforms.

Dates and versions

hal-01494085 , version 1 (22-03-2017)

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Sergio Valente, Zhanjie Xu, Emilie Bana, Clemens Zwergel, Antonello Mai, et al.. Reactivity of 4-Vinyl-2H-1-benzopyran-2-ones in Diels-Alder Cycloaddition Reactions: Access to Coumarin-Based Polycycles with Cdc25 Phosphatase-Inhibiting Activity. European Journal of Organic Chemistry, 2013, 14, pp.2869-2877. ⟨10.1002/ejoc.201201736⟩. ⟨hal-01494085⟩
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