User menu

Accès à distance ? S'identifier sur le proxy UCLouvain

Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

Primary tabs

Pospisil, Jiri [UCL] Potacek, Milan [Masaryk University]

We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2007
Language Anglais
Journal information "Tetrahedron" - Vol. 63, no. 2, p. 337-346 (2007)
Peer reviewed yes
Publisher ELSEVIER
issn 0040-4020
Publication status Publié
Affiliations Masaryk University - Department of chemistry
UCL - Autre
Keywords Intramolecular cycloaddition ; Azomethine ylides ; Solvent-freesynthesis ; Microwave-assisted synthesis ; 1,3-dipolar cycloaddition
Links
Bibliographic reference Pospisil, Jiri ; Potacek, Milan. Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations . In: Tetrahedron, Vol. 63, no. 2, p. 337-346 (2007)
Permanent URL http://hdl.handle.net/2078/69775