Some Transformations of 2-(Chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one

The condensation of 1-amino-3,3-dimethyl-3,4-dihydronaphthalene-2-carbonitrile with chloroacetyl chloride afforded chloro- N -(2-cyano-3,3-dimethyl-3,4-dihydronaphthalen-1-yl)acetamide which underwent cyclization to 2-(chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[ h ]quinazolin-4(3 H )-one. The latter reacted with various nucleophiles (alkali metal alkoxides, piperazine, 2-sulfanylethanol) to give 2-(alkoxymethyl)-, 2-(piperazin-1-ylmethyl)-, and 2-{[(2-hydroxyethyl)sulfanyl]methyl}-5,5-dimethyl-5,6-dihydrobenzo[ h ]quinazolin- 4(3 H )-ones. The condensation of 2-(chloromethyl)benzo[ h ]quinazoline with 2-thioxo derivatives of quinazoline and benzo[ h ]quinazolines led to the formation of bis-quinazolines in which 5,5-dimethyl-5,6- dihydrobenzo[ h ]quinazolin-4(3 H )-one fragment is linked to quinazoline or benzo[ h ]quinazoline system through a CH 2 S bridge.