N-(α-ketoacyl)anthranilic acids reacted with phenylhydrazinium chloride in boiling acetic acid to afford 2-(indol-2-carboxamido)benzoic acids in good to excellent yields and 2-indolyl-3,1-benzoxazin-4-ones as by-products. The formation of the latter products could easily be suppressed by a hydrolytic workup. Alternatively, by increasing the reaction temperature and/or time, 2-indolyl-3,1-benzox...

Occurrence and localization of novel antimicrobial and antifeeding compounds in wheat, 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) and 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), and their glucosides, were examined by staining wheat plants (Triticum aestivum L.) in the juvenile stage of growth by ferric chloride. The methanol extracts of the stained plant tissues gave a characteristic...

DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) is the main hydroxamic acid isolated from maize extracts. It inhibited reversibly ATP synthesis, Pi-ATP exchange reaction and ATPase activity in submitochondrial particles from bovine heart. Half-maximal effects were obtained with 4, 2, and 6 mM DIMBOA respectively. At higher concentrations it also inhibited mitochondrial electron transport ...

Treating 2-chloro-4-(4-chlorophenyl)-6-methylbenzo[d]-3,1-oxazinium hexachloroantimonate (1) with one equivalent of alcohol or mercaptane led, after hydrolysis with aq. NaOH, to the formation of 4,4-disubstituted-1,4-dihydro-2H-6-methyl-3,1-benzoxazin-2-ones (3). Large excess addition of alcohol afforded either 4’-chloro-2-isocyanato-5-methylbenzophenone disubstitutedketal (4) or N-{2[(4-chloro...

2-[2-(2,6-Dichlorophenyl)amino]phenylmethyl-3-{4-[(substituted phenyl)amino]-1,3-oxazol-2-yl)-7-chloroquinazolin-4(3H)ones 5a-o have been prepared from 2-[(2,6-dichloro phenyl)amino]phenyl acetic acid 1, which was converted to acid chloride 2 and cyclized with anthranilic acid afforded benzoxazin-4(H)ones 3. Further reaction with urea gave carboxamide-7-chloroquinazolin-4(3H)ones 4 cyclized wit...