Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
(2003) In Tetrahedron 59(7). p.1033-1048- 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 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... (More)
- 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. (Less)
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https://lup.lub.lu.se/record/120934
- author
- Bergman, J ; Engqvist, R ; Stålhandske, Claes-Ivar LU and Wallberg, H
- organization
- publishing date
- 2003
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- diazepines, indoles, quinolinones
- in
- Tetrahedron
- volume
- 59
- issue
- 7
- pages
- 1033 - 1048
- publisher
- Elsevier
- external identifiers
-
- wos:000180906000012
- scopus:0037429056
- ISSN
- 0040-4020
- DOI
- 10.1016/S0040-4020(02)01647-2
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Polymer and Materials Chemistry (LTH) (011001041)
- id
- a8c1de52-9511-4583-905f-69f10d325917 (old id 120934)
- date added to LUP
- 2016-04-01 16:13:19
- date last changed
- 2022-01-28 18:12:10
@article{a8c1de52-9511-4583-905f-69f10d325917,
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 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.}},
author = {{Bergman, J and Engqvist, R and Stålhandske, Claes-Ivar and Wallberg, H}},
issn = {{0040-4020}},
keywords = {{diazepines; indoles; quinolinones}},
language = {{eng}},
number = {{7}},
pages = {{1033--1048}},
publisher = {{Elsevier}},
series = {{Tetrahedron}},
title = {{Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine}},
url = {{http://dx.doi.org/10.1016/S0040-4020(02)01647-2}},
doi = {{10.1016/S0040-4020(02)01647-2}},
volume = {{59}},
year = {{2003}},
}