Abstract
Ketone carbanion reacted as nucleophilic reagent with 1-chloroisoquinoline (II) and 4-chloroquinazoline (III). The reaction of II in the presence of sodium amide with acetophenone, propiphenone, acetone, 3-pentanone, 2-butanone, 2-pentanone, 3-methyl-2-butanone, 4-methyl-2-pentanone, and cyclopentanone respectively afforded 2-(1-isoquinolinyl) acetophenone (B-1), 2-(1-isoquinolinyl) propiophenone (B-2), 1-(1-isoquinolinyl)-2-propanone (B-3), 2-(1-isoquinolinyl)-3-pentanone (B-4), 2-(1-isoquinolinyl)-2-butanone (B-5), 1-(1-isoquinolinyl)-2-pentanone (B-6), 1-(1-isoquinolinyl)-3-methyl-2-butanone (B-7), 1-(1-isoquinolinyl)-4-methyl-2-pentanone (B-8) and 2-(1-isoquinolinyl) cyclohexanone (B-9). Similarly, the reaction of III with acetophenone, 2-methylpropiophenone, acetone, and cyclopentanone afforded respectively 2-(4-quinazolinyl) acetophenone (C-1), 2-(4-quinazolinyl)-2-methylpropiophenone (C-2), 1-(4-quinazolinyl)-2-propanone (C-3), and 2-(4-quinazolinyl) cyclopentanone (C-6). The reaction with propiophenone and 3-pentanone gave 4-ethylquinazoline (D-1), with butyrophenone and cyclohexanone respectively afforded 4-propylquinazoline (D-2) and 4-quinazolinehexanoic acid (D-3). The reaction with 2-butanone gave 1-(4-quinazolinyl)-2-butanone (C-4) and D-1, with 2-pentanone afforded 1-(4-quinazolinyl)-2-pentanone (C-5) and D-2. It was thereby concluded that the reaction of II and III with ketone carbanion formed the carbon-carbon bond accompanied with the elimination of chloro ion.
