7671-90-1Relevant articles and documents
Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
Bergman, Jan,Engqvist, Robert,St?lhandske, Claes,Wallberg, Hans
, p. 1033 - 1048 (2007/10/03)
Reflux of equimolecular amounts 2-aminobenzylamine and isatins in acetic acid produced indolo[3,2-c]quinolin-6-ones in good yields. A proposed mechanism involving initial formation of a spiro compound is given. This isolable intermediate subsequently rearranges via a sequential isocyanate ring opening and a cyclisation process to a urea derivative which finally cyclized to the indolo[3,2-c]quinolin-6-ones. The urea derivative could be prepared separately and cyclized selectively to indolo[3,2-c]quinolin-6-one. Reaction of N-acetylisatin with 2-aminobenzylamine at room temperature yielded the 1,4-benzodiazepinone 3-(2-acetamidophenyl)-1,5-dihydro-1,4-benzodiazepin-2-one whereas its isomer 2(2-acetamidophenyl)-4,5-dihydro-1,4-benzodiazepin-3-one was obtained from 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide in acetic acid at room temperature. The previously unknown linear isomer of indolo[3,2-c]quinolin-6-one, i.e. indolo[2,3-b]quinolin-11-one, has been prepared by thermal (260°C) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxylate.
SEMICARBAZONES AND THIOSEMICARBAZONES OF THE HETEROCYCLIC SERIES. XLVII. ACYLATION OF ISATIN
Tomchin, A. B.,Fradkina, S. P.,Krylova, I. M.,Khromenkova, Z. A.
, p. 2163 - 2172 (2007/10/02)
Contrary to previous data, the acylation of isatin by carboxylic acid anhydrides in the presence of perchloric acid leads to the formation not of the O-acyl derivatives but of the N-acyl derivatives, which have a noncoplanar structure.Their transformation into isatin hydrazone and oxime is due to hydrolysis of the N-acyl group.In alcohol solutions the N-acylisatins rapidly open the five-membered ring with the addition of an alcohol molecule.