4 -Quinazolones 4-hydroxy

In contrast to the 3-amino derivatives, 3-hydroxy-2,l-benzisoxazoles are relatively labile. With nitrous acid they undergo ring fission to anthranilic add. Its 3-acetoxy derivative (258) reacts with primary amines to form the quinazolone (259) (67AHC(8)277, p. 297). 

Febrifugine, 3-[3-<3-Hydroxy-2-piperidinyt)-2-oxopropyl]-4<3H)-quinazolinone 3-[3-(3-hydroxy-2-piperid- l /cu et >ttyl]-4 3Hi.quina-,ohnone 3-[0-keto-y-(3-hydroxy-2-piperidy])propyl]-4-quinazolone (3-dichrome C,(H,-... 

Alkoxymethyl-4-hydroxy-3,4-dihydro-2(lH)-quinazolones from 4,5-epoxy-l,3,4,5-tetrahydro-2H-l,4-benzodiazepin-2-ones... 

An ethanolic soln. of an/iy ro-5-hydroxy-3-hydroxymethyl-l-methylpyridazinium hydroxide irradiated at room temp, under Ng with the Pyrex-filtered light of a 100 w. high-pressure Hg-arc lamp -> 3-methyl-6-hydroxymethyl-4(3H)-pyrimi-dinone. Y 75%. F. e. s. Y. Maki et al., Tetrah. Let. 1974, 4107 4(3)-quinazolones from 4-hydroxycinnolinium betaines s. D. E. Ames, S. Chandrasekhar, and R. Simpson, Soc. Perkin I 1975, 2035. 

Baker BR, Schaub RE, McEvoy FJ, Williams JH (1952) An antimalarial alkaloid from hydrangea. xii. synthesis of 3-[P-keto-y-(3-hydroxy-2-piperidyl) propyl]-4-quinazolone, the alkaloid. JOig Chem 17 132-140... 

---