Aromatic heterocyclic compounds are known as useful organic materials possessing principle molecular structures for important function of record and display of information.
In this study, novel and convenient methods for synthesis of some benzoheterocyclic compounds from easily available 2-substituted nitrobenzenes were successfully developed through electroreduction, zinc-promoted reduction, reductive carbonylation, and acid-catalyzed intermolecular cyclization.
Thus, useful aromatic heterocyclic compounds, including oxyindoles, 1, 4-benzodiazepinones, 3, 1-dihydrooxazinones, and pridone carboxylic acid derivatives, were efficiently prepared from easily available 2-chloronitrobenzenes and 2-nitrobenzoic acids through electroreduction and zinc-promoted reducton. Furthermore, facile one-pot synthesis of benzazolones, such as benzimidazolones, benzoxazolones and benzthiazolones, and hydroxycoumarines was originally developed by sufur-assisted reductive carbonylation of 2-substituted nitrobenzenes and 2-hydroxylacetophenone, respectively. Finally, acid-catalyzed reaction of propargylic and allylic alcohols with ringsubstituted thiophenols led to selective intermolecular cycloaddition to give readily tetrahydrobenzothiepines and thiochromanes, respectively.
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