Novel pyrrolo[1,2-a][3.1.6]benzothiadiazocine ring synthesis. Unusual Truce-Smiles type rearrangement of 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfonyl(or sulfinyl)}acetone
| dc.contributor.author | Kimbaris, A. | en |
| dc.contributor.author | Cobb, J. | en |
| dc.contributor.author | Tsakonas, G. | 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/123456789/8617 | |
| dc.rights | Default Licence | - |
| dc.subject | pyrroles | en |
| dc.subject | pyrrolobenzothiadiazocines | en |
| dc.subject | cyclisation | en |
| dc.subject | reduction | en |
| dc.subject | truce-smiles rearrangement | en |
| dc.subject | reverse-transcriptase inhibitors | en |
| dc.subject | pyrrolyl aryl sulfones | en |
| dc.subject | heterocyclic-systems | en |
| dc.subject | 5,5-dioxide | en |
| dc.subject | derivatives | en |
| dc.title | Novel pyrrolo[1,2-a][3.1.6]benzothiadiazocine ring synthesis. Unusual Truce-Smiles type rearrangement of 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfonyl(or sulfinyl)}acetone | en |
| heal.abstract | Reaction of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfonyl} acetone with sodium hydroxide with or without zinc gave 1-(2-nitrophenyl)(1H-pyrrol-2-ylsulfonyl)methane by a Truce-Smiles type of transformation and 1-(2-nitrophenyl)-2-methylsulfonylpyrrole by deacetylation. Similar treatment of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfinyl}acetone gave only 1-(2-nitro-phenyl)(1H-pyrrol-2-ylsulfinyl)methane. 1-{[1-(2-Nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetone, 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}-1-phenylethan-1-one or 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetonitrile were reductively cyclised with sodium borohydride and 5% palladium-on-carbon into 6-methyl(or phenyl)-5,6-dihydro-7H-pyrrolo[1,2-a][3.1.6]benzothiadiazocin-7-ol or 6-amino-5H-pyrrolo[1,2-a][3.1.6]benzothiadiazocine-7-oxide, respectively. (C) 2004 Elsevier Ltd. All rights reserved. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | DOI 10.1016/j.tet.2004.07.036 | - |
| heal.identifier.secondary | <Go to ISI>://000223935100005 | - |
| heal.identifier.secondary | http://ac.els-cdn.com/S0040402004011597/1-s2.0-S0040402004011597-main.pdf?_tid=d14247a2-34ac-11e3-b43e-00000aab0f27&acdnat=1381740440_c92b877b397b84078e419318666ebed4 | - |
| heal.journalName | Tetrahedron | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2004 | - |
| 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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