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

被引:90
作者
Bergman, J
Engqvist, R
Stålhandske, C
Wallberg, H
机构
[1] Sodertorn Univ Coll, Karolinska Inst, Novum,CNT, Dept Biosci,Unit Organ Chem, SE-14157 Huddinge, Sweden
[2] Sodertorn Univ Coll, SE-14104 Huddinge, Sweden
[3] Ctr Chem, Dept Inorgan Chem 2, SE-22100 Lund, Sweden
[4] Royal Inst Technol, Dept Organ Chem, SE-10044 Stockholm, Sweden
关键词
diazepines; indoles; quinolinones;
D O I
10.1016/S0040-4020(02)01647-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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-2one 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-blquinolin-11-one, has been prepared by thermal (260degreesC) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxyl ate. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1033 / 1048
页数:16
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