e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

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

J Bergman, R Engqvist, C Stålhandske, H Wallberg

Index: Bergman, Jan; Engqvist, Robert; Stalhandske, Claes; Wallberg, Hans Tetrahedron, 2003 , vol. 59, # 7 p. 1033 - 1048

Full Text: HTML

Citation Number: 96

Abstract

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 ...

isatin Structure

o-Phenylenediamine Structure

o-Phenylenediamine

~80%

2(1H)-Quinoxalinone,3-(2-aminophenyl)- Structure

2(1H)-Quinoxali...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

2-AMINOBENZYLAMINE Structure

2-AMINOBENZYLAMINE

~60%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

1,2,3,4-tetrahydroquinazoline-5-methyl-2-spiro-3'-1H-indolin-2-one Structure

1,2,3,4-tetrahy...

~76%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

Sodium cyanide Structure

2-(2-amino-5-methylphenyl)-1H-indole Structure

2-(2-amino-5-me...

~71%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

N/A Structure

~62%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

Ethanone, 1-(2-amino-5-methylphenyl)- (9CI) Structure

Ethanone, 1-(2-...

~%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

2-AMINOBENZYLAMINE Structure

2-AMINOBENZYLAMINE

~%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

2-(2-amino-5-methylphenyl)-1H-indole Structure

2-(2-amino-5-me...

~%

2-methyl-5,11-dihydroindolo[3,2-c]quinolin-6-one Structure

2-methyl-5,11-d...

11-chloro-6H-indolo[2,3-b]quinoline Structure

11-chloro-6H-in...

~90%

5h-quinindoline Structure

5h-quinindoline

Methyl 3-indolecarboxylate Structure

Methyl 3-indole...

~%

5h-quinindoline Structure

5h-quinindoline

Structure

~%

5h-quinindoline Structure

5h-quinindoline

5,6-dihydro-11H-indolo[2,3-b]quinolin-11-one Structure

5,6-dihydro-11H...

~%

5h-quinindoline Structure

5h-quinindoline

N/A Structure

~%

5h-quinindoline Structure

5h-quinindoline

11-chloro-5-acetylindolo[2,3-b]quinoline Structure

11-chloro-5-ace...

~%

5h-quinindoline Structure

5h-quinindoline

1-methylisatin Structure

2-AMINOBENZYLAMINE Structure

2-AMINOBENZYLAMINE

~81%

5-methyl-11H-indolo[3,2-c]quinolin-6-one Structure

5-methyl-11H-in...

2-AMINOBENZYLAMINE Structure

2-AMINOBENZYLAMINE

~%

5-methyl-11H-indolo[3,2-c]quinolin-6-one Structure

5-methyl-11H-in...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

5-methyl-11H-indolo[3,2-c]quinolin-6-one Structure

5-methyl-11H-in...

isatin Structure

2-AMINOBENZYLAMINE Structure

2-AMINOBENZYLAMINE

~95%

5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one Structure

5,11-dihydro-6H...

1,2,3,4-tetrahydroquinazoline-2-spiro-3'-1H-indolin-2-one Structure

1,2,3,4-tetrahy...

~97%

5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one Structure

5,11-dihydro-6H...

2-(2-Aminophenyl)indole Structure

2-(2-Aminopheny...

Sodium cyanide Structure

~79%

5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one Structure

5,11-dihydro-6H...

undec-4-yn-1-ol Structure

undec-4-yn-1-ol

~70%

5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one Structure

5,11-dihydro-6H...