1,3-dipolar cycloaddition route to nitrogen heterocyclic triones

Authors
Jones, RCF Bhalay, G Carter, PA Duller, KAM Dunn, SH
Citation
Rcf. Jones et al., 1,3-dipolar cycloaddition route to nitrogen heterocyclic triones, J CHEM S P1, (7), 1999, pp. 765-776
Citations number
59
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
7
Year of publication
1999
Pages
765 - 776
Database
ISI
SICI code
0300-922X(19990407):7<765:1CRTNH>2.0.ZU;2-#
Abstract
1,3-Dipolar cycloadditiqn of nitrile oxides, formed in situ by dehydration of primary nitro compounds, with pyrrolidine enamines of protected gamma- o r delta-amino-beta-keto esters affords isoxazole-4-carboxylates; these unde rgo lactam formation and N-O bond cleavage to afford 3-acyltetramic acids a nd 3-acyl-4-hydroxypyridin-2-ones.