Abstract
The construction of the biologically interesting chromone skeleton was realized by PhIO-mediated dehydrogenation of chromanones under mild conditions. Interestingly, this method also found application in the synthesis of the naturally occurring frutinone A.
Highlights
The chromone system and its derivatives are an important class of heterocyclic compounds, the skeleton of which widely exists in a variety of natural products and medicinal agents [1,2,3]
Flavoxate [15,16] is a chromone derivative that was employed as an anticholinergic agent for its antimuscarinic effects [3,17]; apigenin can function as an antiviral drug for the treatment of HIV [18,19], cancer [20,21,22], and other viral infections [23]; pranlukast [24] can be used in the treatment of allergic rhinitis [25] and asthma [26]; and Beilstein J
We initially studied the feasibility of converting chromanone ethyl 4-oxo-2-phenylchromane-3-carboxylate (1a) to chromone 2a via PhIO-mediated dehydrogenation
Summary
The chromone system and its derivatives are an important class of heterocyclic compounds, the skeleton of which widely exists in a variety of natural products and medicinal agents [1,2,3]. (IBX) could effectively dehydrogenate chromanones to chromones (Scheme 1d, method 1) [63]. Active MnO2 was found useful in the oxidative dehydrogenation of chromanones at a relatively high temperature of 110 °C (Scheme 1d, method 2) [64,65].
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