REACTIONS OF CARBON-NUCLEOPHILES WITH ACETYLENIC ESTERS AND KETONES

Cyanoacetanilide (1) reacted with 3-phenyl-1-aryl-prop-2-yn-1-ones (2a -c) in the presence of sodium pellets in dry benzene to give the corre sponding 3-cyanopyrid-2-ones (3a-c) and the aminopyrid-2-ones (4a,b). Similarly 1 reacted with methyl 3-arylprop-2-ynoates (2d,e) to give th e 5-cyanopyrid-2-ones (7a,b) and the pyran-2-ones (8). On the other ha nd, 6-chloro-3-cyano-4-methylcoumarin (9) reacted with 2a-c,e to give the corresponding 3-amino-4-aroyl or carbomethoxy-8-chloro-5-arylbenzo [c]coumarin (10a-d) as well as the propenylcoumarins (11) and the benz o[c]coumarins (12). In all cases the reactions seem to take place via Michael addition.