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https://hdl.handle.net/1822/57413
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Campo DC | Valor | Idioma |
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dc.contributor.author | Hall, R. J. | por |
dc.contributor.author | Dharmasena, P. | por |
dc.contributor.author | Marchant, J. | por |
dc.contributor.author | Campos, Ana M. F. Oliveira | por |
dc.contributor.author | Queiroz, Maria João R. P. | por |
dc.contributor.author | Raposo, M. Manuela M. | por |
dc.contributor.author | Shannon, P. V. R. | por |
dc.date.accessioned | 2018-12-19T11:44:00Z | - |
dc.date.available | 2018-12-19T11:44:00Z | - |
dc.date.issued | 1993 | - |
dc.identifier.citation | Hall, R.J.; Dharmasena, P.; Marchant, J.; Oliveira-Campos, A. M. F.; Queiroz, M. J. R. P.; Raposo, M. M. M.; Shannon, P. V. R. A flexible approach to pyrido[4,3-b]carbazoles. The syntheses of 5-methyl-8,10-dimethoxy; 5,11-dimethoxy-7,10-dimethyl and 9-fluoro-5,11-dimethylpyrido[4,3-b]carbazoles by variations of the type D route. J. Chem. Soc. Perkin 1 1993, 1879-1889 | por |
dc.identifier.issn | 0300-922X | por |
dc.identifier.uri | https://hdl.handle.net/1822/57413 | - |
dc.description.abstract | Syntheses of three different pyridocarbazoles are described. Palladium acetate oxidation of 4-cyano-N-(3,5-dimethoxyphenyl)-2-methylaniline 19 and reduction of the resultant 3-cyano-4,6-dimethoxy-1-methylcarbazole 23 with diisobutylaluminium hydride gave the corresponding formylcarbazole 22. Modified Pomeranz–Fritsch cyclisation then gave, as the major product, 8,10-dimethoxy-5-methylpyrido[4,3-b]carbazole 32. Acid-catalysed condensation of 4,7-dimethoxyindole with hexane-2,5-dione gave 5,8-dimethoxy-1,4-dimethylcarbazole 37 which underwent an atypical regiospecific formylation to give 3-formyl-1,4-dimethoxy-5,8-dimethylcarbazole 39. This was converted by standard methods into 5,11-dimethoxy-7,10-dimethylpyrido[4,3-b]carbazole 7. The cyclisation reactions of the formylcarbazoles 26 and 43 were studied by 1H NMR spectroscopy which enabled the isolation of intermediate N-tosyl-1,2-dihydropyridocarbazoles. An unambiguous synthesis of 9-fluoroellipticine 8 is described from 5-fluoroindole for the first time. | por |
dc.description.sponsorship | We thank the Wellcome Research Laboratories, Beckenham, Kent for a CASE award (to R. J. H.), the SERC for a quota award (to J. M.), the Instituto National de Investigacao Cientifica, Portugal for support (to M. J. R. P. Q.), Amersham International plc and the Overseas Research Students Awards Scheme for scholarships (to P. M. D.) and the British Council (Treaty of Windsor Award). | por |
dc.language.iso | eng | por |
dc.publisher | Royal Society of Chemistry | por |
dc.rights | openAccess | por |
dc.rights.uri | http://creativecommons.org/licenses/by-nc/4.0/ | por |
dc.subject | Synthesis | por |
dc.subject | Pyridocarbazoles | por |
dc.subject | Ellipticines | por |
dc.subject | Palladium acetate oxydation | por |
dc.subject | Diphenylamine precursors | por |
dc.subject | Pomeranz–Fritsch cyclisation | por |
dc.subject | Carbazole | por |
dc.subject | Formylation | por |
dc.subject | Acid-catalysed condensation | por |
dc.title | A flexible approach to pyrido[4,3-b]carbazoles. The syntheses of 8,10-dimethoxy-5-methyl-, 5,11-dimethoxy-7,10-dimethyl- and 9-fluoro-5,11-dimethylpyrido[4,3-b]carbazoles by variations of the 'type D' route | por |
dc.type | article | por |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | https://pubs.rsc.org/en/content/articlepdf/1993/p1/p19930001879 | por |
oaire.citationStartPage | 1879 | por |
oaire.citationEndPage | 1889 | por |
oaire.citationIssue | 16 | por |
dc.identifier.doi | 10.1039/P19930001879 | por |
dc.subject.fos | Ciências Naturais::Ciências Químicas | por |
dc.description.publicationversion | info:eu-repo/semantics/publishedVersion | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | Journal of the Chemical Society, Perkin Transactions 1 | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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J. CHEM. SOC. PERKIN TRANS. I 1993, 1879-1889.pdf | Manuscrito | 1,49 MB | Adobe PDF | Ver/Abrir |
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