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Titolo:
INTRAMOLECULAR CYCLIZATION OF AZIDES BY IMINIUM SPECIES - A NOVEL METHOD FOR THE CONSTRUCTION OF NITROGEN HETEROCYCIES UNDER VILSMEIER CONDITIONS
Autore:
MAJO VJ; PERUMAL PT;
Indirizzi:
CENT LEATHER RES INST,DIV ORGAN CHEM CHENNAI 600020 INDIA CENT LEATHER RES INST,DIV ORGAN CHEM CHENNAI 600020 INDIA
Titolo Testata:
Journal of organic chemistry
fascicolo: 21, volume: 63, anno: 1998,
pagine: 7136 - 7142
SICI:
0022-3263(1998)63:21<7136:ICOABI>2.0.ZU;2-M
Fonte:
ISI
Lingua:
ENG
Soggetto:
ONE-POT SYNTHESIS; VINYL AZIDES; FUSED PYRIDINES; SCHMIDT REACTION; PHOTOCHEMICAL DECOMPOSITION; 1,3-DIPOLAR CYCLOADDITION; HAACK REAGENT; QUINOLINES; ROUTE; DERIVATIVES;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
123
Recensione:
Indirizzi per estratti:
Citazione:
V.J. Majo e P.T. Perumal, "INTRAMOLECULAR CYCLIZATION OF AZIDES BY IMINIUM SPECIES - A NOVEL METHOD FOR THE CONSTRUCTION OF NITROGEN HETEROCYCIES UNDER VILSMEIER CONDITIONS", Journal of organic chemistry, 63(21), 1998, pp. 7136-7142

Abstract

An unprecedented attack of the azide functionality by iminium species, generated in situ under Vilsmeier conditions, provided a novel routefor the construction of nitrogen heterocycles. Thus, the treatment of2-azidoacetophenones with Vilsmeier reagent under reflux conditions gave 5-aryloxazole-4-carboxaldehydes. One-pot synthesis of oxazole carboxaldehydes from 2-bromoacetophenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The susceptibility of the carbonyl group to undergo chloroformylation at room temperaturewithout affecting the azide function was exploited to provide an attractive scheme for the synthesis of alpha-azido-beta-chlorovinyl azidesfrom phenacyl azides. The synthesis of a series of N-aryl hloro-2-(dimethylamino)imidazole-4-carboxaldehydes was accomplished by the Vilsmeier cyclization of N-aryl-2-azidoacetamides. The possible mechanisms for the reactions are also discussed.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 15:04:31