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Titolo:
SYNTHESIS OF INDOLE SUBSTITUTED DIHYDRO-ISOXAZOLES AND TETRAHYDRO-ISOXAZOLES VIA 1,3-DIPOLAR CYCLOADDITIONS OF C-(1-METHYLINDOL-2-YL)-N-METHYLNITRONE WITH UNSATURATED CARBONYL DERIVATIVES AND A STUDY OF THEIR ACID-INDUCED INTRAMOLECULAR CYCLIZATIONS
Autore:
MALAMIDOUXENIKAKI E; STAMPELOS XN; COUTOULIARGYROPOULOU E; CARDIN CJ; TEIXEIRA S; KAVOUNIS CA;
Indirizzi:
ARISTOTELIAN UNIV THESSALONIKI,DEPT CHEM GR-54006 THESSALONIKI GREECE UNIV READING,DEPT CHEM READING RG4 9BB BERKS ENGLAND ARISTOTELIAN UNIV THESSALONIKI,DEPT PHYS GR-54006 THESSALONIKI GREECE
Titolo Testata:
Journal of the Chemical Society. Perkin transactions. I
fascicolo: 6, , anno: 1997,
pagine: 949 - 957
SICI:
0300-922X(1997):6<949:SOISDA>2.0.ZU;2-J
Fonte:
ISI
Lingua:
ENG
Soggetto:
CYCLO-ADDITIONS; YUEHCHUKENE; NITRONES; ANALOGS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
29
Recensione:
Indirizzi per estratti:
Citazione:
E. Malamidouxenikaki et al., "SYNTHESIS OF INDOLE SUBSTITUTED DIHYDRO-ISOXAZOLES AND TETRAHYDRO-ISOXAZOLES VIA 1,3-DIPOLAR CYCLOADDITIONS OF C-(1-METHYLINDOL-2-YL)-N-METHYLNITRONE WITH UNSATURATED CARBONYL DERIVATIVES AND A STUDY OF THEIR ACID-INDUCED INTRAMOLECULAR CYCLIZATIONS", Journal of the Chemical Society. Perkin transactions. I, (6), 1997, pp. 949-957

Abstract

C-(1-Methylindol-2-yl)-N-methylnitrone 4 reacts with carbonyl-substituted dipolarophiles to afford the isoxazolidines 6-9 and the 3,4-dihydroisoxazole 10 in high yields and with low to moderate regio- and stereo-selectivity. The indolyl-isoxazolidines 6a-c,e,f bearing a 5-methoxycarbonyl or a 5-carboxy substituent in a cis relationship to the 3-indolyl group undergo acid-induced intramolecular acylation to afford the bridged indole derivatives 11a-d. The acid-induced intramolecular cyclization products of the isoxazolidines 7a,b that lack a cis 5-methoxycarbonyl substituent or the isoxazolidines 8c,f that have no 5-methoxycarbonyl substituent are the enamine (reversible arrow inine) 12 and/or the diketone 13 depending on the reaction conditions. The spectral elucidation of the products is discussed and mechanistic schemes to explain the formation of the products are suggested. An X-ray structure determination has been carried out on product 11a.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/11/20 alle ore 03:28:07