Harry Louis Yale

Substituted 2, 3-dihydro-4(1h)-quinazolinones

Details are given for the reaction of isatoic anhydrides with different primary aromatic amines to give several new N-aryl-o-aminobenzamides. The latter were annulated with a variety of dialkyl and alkyl aryl ketones to give 2,3-dihydro-4(1H)quinazolinones. Several novel and efficient procedures for effecting the cyclization are described.

Derivatives of 2,3-Dihydrocyclopenta[d] pyrido[1,2-a] pyrimidin-10(1H)one

The annulation of 2-amino-3-hydroxy-, 2-amino-3-carboxy-, and 2-amino-3-methylpyridine with ethyl cyelopenlanone-2-earboxylate led to the 5-hydroxy-, 2, 5-carboxy-, 3, and 5-methyl-, 4, derivatives of the 2,3-dihydrocycloperita[d]pyrido[1,2-a]pyrimidin-10(1H) one heterocycle. Alkylation of 2 with α-bromotolue, ne gave the 5-benzyloxy derivative.

THE REACTION OF 2‐ACETOACETAMIDOPYRIDINES WITH PHOSGENE. A ROUTE TO NOVEL 3‐ACETYL‐2‐CHLORO‐4H‐PYRIDO(1,2‐A)PYRIMIDIN‐4‐ONES

2-(Acetoacetamido)pyridine, 1, and its 5-methyl derivative, 2, with phosgene, gave 3-acetyl-2-chloro-4H-pyrido[1,2-a]pyrimidin-4-one, 5, and 3-acetyl-2-chloro-7-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one, 6, respectively. The structures of these compounds followed from their elemental analyses, and interpretations of their uv, ir, pmr, and X-ray spectra. An alternative route to 5 and 6, which sought first to react 1 and 2 with methyl - and benzyl chloroformates, was unsuccessful, and led, instead, to elimination of the acetoacetyl group with concomitant formation of the carbamate derivatives, 10 and 11.