CONDENSATION OF ETHYL ACETOACETATE WITH NAPHTHALENE-DIOLS - THE SYNTHESIS OF SOME NOVEL COUMARINS AND CHROMONES .1.

In Simonis reaction with ethyl acetoacetate naphthalene-2,6-diol gives 8-hydroxy-3-methyl-1 H-naphtho[2,1-b]pyran-l-one and naphthalene-2,7-diol gives the related 9-hydroxy isomer. In Pechman reactions, the former diet yields a coumarin, 8-hydroxy-1-methyl-3H-naphtho[2,1-b]-pyran-3-one, with the corresponding orientation, but the latter diol gives a coumarin, 8-hydroxy-4-methyl-2H-naphtho[2,3-b]-pyran-2-one, with an unusual linear annelation pattern.