Anhydridbildung bei einer Diaminomonooxys�ure

The Chemistry of Isatin.

“…A7-Methylisatin and A7-ethylisatin can be prepared most conveniently by alkylating isatin by means of methyl sulfate and ethyl sulfate, respectively (43,122,242,244).…”

“…The reactions of isatin and its derivatives with Grignard reagents have been studied by Kohn and coworkers (238,239,242,243,244), by Myers and Lindwall (310), and by other workers (205,369,370,373,381,387,389) Grignard reagents isatin yields the corresponding 3-alkyl (or aryl)-3-hydroxyoxindoles (I). Kohn (243) found that when phenylmagnesium bromide and IV-methylisatin were allowed to react in equimolecular proportions the analogous l-methyl-3-phenyl-3-hydroxyoxindole (II) was obtained.…”

“…Reaction with hydroxylamine, phenylhydrazine, and aromatic amines Isatin reacts with hydroxylamine to give isatin ß-oxime (23,45,59,129,130,159,243,249,280,414). Isatin ß-oxime is identical with nitrosooxindole and can be prepared by treating oxindole with nitrous acid (24,46,129,148,149,243). Direct reaction of isatin and hydroxylamine gives only the ß-oxime (249).…”

“…152,240,241,242,244,268,382,385,403). On the other hand Heller has proposed a quinhydrone structure (II) for isatide (174, h i b i t e d .…”

The Chemistry of Oxindole.

“…3-Alkyl-3-hydroxyoxindoles (IX) are readily prepared by the action of Grignard reagents on isatin (85,115,116,119,120,121,154,174,175,176,182,186,187). (For other syntheses of 3-phenyl-3-hydroxyoxindole see references 13 and R ---COH /CO NCH».…”