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Reactivity of 4‐Vinyl‐2 H ‐1‐benzopyran‐2‐ones in Diels–Alder Cycloaddition Reactions: Access to Coumarin‐Based Polycycles with Cdc25 Phosphatase‐Inhibiting Activity
Author(s) -
Valente Sergio,
Xu Zhanjie,
Bana Emilie,
Zwergel Clemens,
Mai Antonello,
Jacob Claus,
Meiser Peter,
Bagrel Denyse,
Silva Artur M. S.,
Kirsch Gilbert
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201736
Subject(s) - chemistry , cycloaddition , reactivity (psychology) , coumarin , diene , medicinal chemistry , diels–alder reaction , organic chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology
The reactivity of 4‐(1‐butoxyvinyl)‐2 H ‐chromen‐2‐one ( 1 ) and ( E )‐4‐(2‐butoxyvinyl)‐2 H ‐chromen‐2‐one ( 2 ) as diene in thermal Diels–Alder cycloaddition reactions with several electron‐poor dienophiles is reported. Among several dienophiles used in this study 1,4‐benzoquinone afforded cycloadducts 11‐butoxy‐1 H ‐naphtho[1,2‐ c ]chromene‐1,4,5‐trione ( 3e ) and 1 H ‐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.