7671-90-1

Upstream product

• 574-17-4 1-acetyl-1H-indole-2,3-dione 
• 64-17-5 ethanol 
• 91-56-5 indole-2,3-dione 
• 75-03-6 ethyl iodide 

Downstream Products

• 245-10-3 5H-pyrazino[2,3-b]indole 
• 193959-69-2 3-(2-Amino-phenyl)-1H-pyrazin-2-one 
• 193959-71-6 3-(2-Amino-phenyl)-5-methyl-1H-pyrazin-2-one 
• 193959-72-7 3-(2-Amino-phenyl)-5-ethyl-1H-pyrazin-2-one 
• 193959-65-8 N-[2-(3-Oxo-3,4-dihydro-pyrazin-2-yl)-phenyl]-acetamide 
• 193959-67-0 N-[2-(6-Methyl-3-oxo-3,4-dihydro-pyrazin-2-yl)-phenyl]-acetamide 
• 193959-83-0 3-(2-Amino-phenyl)-1-(2-dimethylamino-ethyl)-1H-pyrazin-2-one 
• 193959-68-1 N-[2-(6-Ethyl-3-oxo-3,4-dihydro-pyrazin-2-yl)-phenyl]-acetamide 
• 193959-81-8 N-{2-[4-(2-Dimethylamino-ethyl)-3-oxo-3,4-dihydro-pyrazin-2-yl]-phenyl}-acetamide 
• 543745-53-5 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide 
• 193959-53-4 N-[2-(6-Methyl-3-oxo-3,4,5,6-tetrahydro-pyrazin-2-yl)-phenyl]-acetamide 
• 81965-08-4 N-[2-(3-Oxo-3,4,5,6-tetrahydro-pyrazin-2-yl)-phenyl]-acetamide 
• 193959-54-5 N-[2-(6-Ethyl-3-oxo-3,4,5,6-tetrahydro-pyrazin-2-yl)-phenyl]-acetamide 

Relevant academic research and scientific papers

Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine

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.

Synthesis of 5H-pyrazino[2,3-b]indoles from indole-2,3-dione derivatives

Reaction of N-acetylindol-2,3-diones with ethylenediamines gave the dihydropyrazinones 11, which could, after dehydrogenation and deacetylation, be transformed to the corresponding 5H-pyrazino[2,3-e]indoles 5. N,N-Dimethylaminoethylation of the anion of 5

SEMICARBAZONES AND THIOSEMICARBAZONES OF THE HETEROCYCLIC SERIES. XLVII. ACYLATION OF ISATIN

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.