Novel synthesis of the pyrrolo[2,1-c][1,4]benzodiazocine ring system via a Dieckmann condensation
| dc.contributor.author | Koriatopoulou, K. | en |
| dc.contributor.author | Karousis, N. | en |
| dc.contributor.author | Varvounis, G. | en |
| dc.date.accessioned | 2015-11-24T16:42:55Z | |
| dc.date.available | 2015-11-24T16:42:55Z | |
| dc.identifier.issn | 0040-4020 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/8620 | |
| dc.rights | Default Licence | - |
| dc.subject | pyrroles | en |
| dc.subject | oxidation | en |
| dc.subject | dieckmann condensation | en |
| dc.subject | pyrrolobenzodiazocine | en |
| dc.subject | derivatives | en |
| dc.subject | cyclization | en |
| dc.title | Novel synthesis of the pyrrolo[2,1-c][1,4]benzodiazocine ring system via a Dieckmann condensation | en |
| heal.abstract | A novel four-step synthesis to the pyrrolo[2,1-c][1,4]benzodiazocine ring system is described. 1H-Pyrrole2-carbaldehyde was alkylated with ethyl or methyl bromoacetate and the resulting ethyl or methyl (2-formyl-1H-pyrrol-1-yl)acetates oxidised with potassium permanganate to the corresponding 1-[(2-ethoxy or methoxy)-2-oxoethyl]-1H-pyrrole-2-carboxylic acids. The latter was converted into their acid chlorides by reaction with thionyl chloride and without isolation transformed into the respective methyl 2-({[1-(2-ethoxy or methoxy-2-oxoethyl)-1H-pyrrol-2-yl]carbonyl}amino)benzoates by reaction with methyl anthranilate. Dieckmann condensation of methyl 2-({[1-(2-methoxy-2-oxoethyl)-1H-pyrrol-2-yl]carbonyl}amino)benzoate provided the pyrrolo[2,1-c][1,4]benzodiazocine. (C) 2008 Published by Elsevier Ltd. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | DOI 10.1016/j.tet.2008.07.029 | - |
| heal.identifier.secondary | <Go to ISI>://000259939000028 | - |
| heal.identifier.secondary | http://ac.els-cdn.com/S0040402008013148/1-s2.0-S0040402008013148-main.pdf?_tid=e5730220-34ac-11e3-b853-00000aab0f6b&acdnat=1381740474_6e0c2b656ce3f088f620fe517c289418 | - |
| heal.journalName | Tetrahedron | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2008 | - |
| heal.publisher | Elsevier | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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