Reduction of 2-and 3-acylpyrroles. A new synthesis of the pyrrolo[1,2-b]cinnolin-10-one ring system from 1-(4-methylphenyl)sulfonyl-1H-pyrrole
| dc.contributor.author | Kimbaris, A. | en |
| dc.contributor.author | Varvounis, G. | en |
| dc.date.accessioned | 2015-11-24T16:46:15Z | |
| dc.date.available | 2015-11-24T16:46:15Z | |
| dc.identifier.issn | 0040-4020 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/9050 | |
| dc.rights | Default Licence | - |
| dc.subject | pyrroles | en |
| dc.subject | reduction | en |
| dc.title | Reduction of 2-and 3-acylpyrroles. A new synthesis of the pyrrolo[1,2-b]cinnolin-10-one ring system from 1-(4-methylphenyl)sulfonyl-1H-pyrrole | en |
| heal.abstract | Reduction of (2-nitrophenyl)(1H-pyrrol-2-yl)methanone 4 with zinc and ammonium chloride gave 5,10-dihydro-pyrrolo[1,2-b]cinnolin-10-one 5 and (2-hydroxylaminophenyl)(1H-pyrrol-2-yl)methanone 6 whereas reduction of 4 with zinc and sodium hydroxide gave only 5. Reaction of (2-nitrophenyl)(1H-pyrrol-3-yl)methanone 10 with zinc and ammonium chloride or zinc and sodium hydroxide afforded (2-nitrosophenyl)(1H-pyrrol-3-yl)methanone 11 and 2-aminophenyl)(1H-pyrrol-3-yl)methanone 12 or 12 as a single product, respectively. Sodium burohydride reduction of (2-nitrophenyl)(1-methyl-1H-pyrrol-2-yl)methanone 13 or (2-nitrophenyl)(1-methyl-1H-3-pyrrolyl)methanone 19 gave a mixture of the corresponding alcohols 15 or 21 and nitroso-ketones 18 or 22. Reduction of alcohols 15 or 21 with zinc and sodium hydroxide afforded nitroso-ketones 18 or 22, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | Doi 10.1016/S0040-4020(00)00922-4 | - |
| heal.identifier.secondary | <Go to ISI>://000165485500019 | - |
| heal.identifier.secondary | http://ac.els-cdn.com/S0040402000009224/1-s2.0-S0040402000009224-main.pdf?_tid=bb5c23e0-34ac-11e3-b7bc-00000aacb35e&acdnat=1381740403_7dcfdab5029db12fb4de0dcc43443d21 | - |
| heal.journalName | Tetrahedron | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2000 | - |
| 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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