1,3-dipolar cycloaddition reactions of o-benzoquinones: An overview

Authors
Nair, V Radhakrishnan, KV Sheela, KC
Citation
V. Nair et al., 1,3-dipolar cycloaddition reactions of o-benzoquinones: An overview, RES CHEM IN, 25(9), 1999, pp. 877-886
Citations number
15
Categorie Soggetti
Chemistry
Journal title
RESEARCH ON CHEMICAL INTERMEDIATES
ISSN journal
09226168 → ACNP
Volume
25
Issue
9
Year of publication
1999
Pages
877 - 886
Database
ISI
SICI code
0922-6168(1999)25:9<877:1CROOA>2.0.ZU;2-8
Abstract
The dipolar cycloaddition reactions of o-benzoquinones exhibiting different reactivity profiles with different dipoles are described. With diazomethan e, the corresponding indazole is formed by the addition to C=C bond, while with mesoionic compounds, novel heterocyclic compounds are obtained. Depend ing on the nature of the substituents on the substrates, benzonitrile oxide s add to both C=C and C=O of o-quinones. Carbonyl ylides afforded highly ox ygenated spirocyclic compounds.