Regioselective synthesis and biological evaluation of: N -substituted 2-aminoquinazolin-4-ones
Journal
Organic and Biomolecular Chemistry
Journal Volume
16
Journal Issue
24
Pages
4482-4494
Date Issued
2018
Author(s)
Liao Z.-Y.
Yeh W.-H.
Liao P.-Y.
Liu Y.-T.
Chen Y.-C.
Chen Y.-H.
Hsieh T.-H.
Lin C.-C.
Lu M.-H.
Chen Y.-S.
Hsu M.-C.
Chien T.-C.
Abstract
The reaction of methyl anthranilates with N-arylcyanamides in the presence of p-TsOH in t-BuOH under reflux afforded predominantly 3-arylquinazolin-4-ones. In contrast, the reaction of the same reactants with TMSCl in t-BuOH at 60 °C followed by the Dimroth rearrangement in aqueous ethanolic sodium hydroxide gave exclusively the regioisomers, 2-(N-arylamino)quinazolin-4-ones. The regioselective synthesis of N-aryl-substituted 2-aminoquinazolin-4-ones can be further applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones.
Publisher
Royal Society of Chemistry
Type
journal article