Quinazolin-4(3<i>H</i>)-ones and 5,6-Dihydropyrimidin-4(3<i>H</i>)-ones from β-Aminoamides and Orthoesters

oleh: Joshua T. Gavin, Joel K. Annor-Gyamfi, Richard A. Bunce

Format: Article
Diterbitkan: MDPI AG 2018-11-01

Deskripsi

Quinazolin-4(3<i>H</i>)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12&#8315;24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110 &#176;C for 12&#8315;72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3<i>H</i>)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and HRMS.