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Titolo:
NITROGEN-HETEROCYCLES FROM FURANS - THE AZA-ACHMATOWICZ REACTION
Autore:
CIUFOLINI MA; HERMANN CYW; DONG Q; SHIMIZU T; SWAMINATHAN S; XI N;
Indirizzi:
RICE UNIV,DEPT CHEM,MS 60,6100 MAIN HOUSTON TX 77005
Titolo Testata:
Synlett
fascicolo: 2, , anno: 1998,
pagine: 105 -
SICI:
0936-5214(1998):2<105:NFF-TA>2.0.ZU;2-7
Fonte:
ISI
Lingua:
ENG
Soggetto:
STEREOSELECTIVE TOTAL SYNTHESES; INTRAMOLECULAR N-ALKYLATION; GLYOXYLIC-ACID DERIVATIVES; PIPERIDINE RING FORMATION; USEFUL BUILDING-BLOCKS; ASYMMETRIC-SYNTHESIS; ELECTROORGANIC CHEMISTRY; GLUCOSIDASE INHIBITORS; FACILE SYNTHESIS; BETA-LACTAMS;
Keywords:
ALKALOIDS; AMINO-ACIDS; AZASACCHARIDES; CARBACEPHEMS; ENZYMES; FURANS; IZIDINES; PIPERIDINES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
93
Recensione:
Indirizzi per estratti:
Citazione:
M.A. Ciufolini et al., "NITROGEN-HETEROCYCLES FROM FURANS - THE AZA-ACHMATOWICZ REACTION", Synlett, (2), 1998, pp. 105

Abstract

The furan nucleus may be considered as a latent 1,4-dicarbonyl group. Expression of this functional equivalence within a generic 2-furylamide results in formation of nitrogen heterocycles in a reaction that may be termed the ''Aza-Achmatowicz rearrangement'', by analogy with similar transformations of furylcarbinols. Aza-Achmatowicz products may be created in enantioselective form by chemoenzymatic methods, and are useful intermediates in the synthesis of novel carbacephems, unusual aminoacids, azasaccharides, piperidine and izidine alkaloids. This Account reviews the most significant aspects of aza-Achmatowicz chemistry.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 21:30:21