ANNULATION OF DIHYDROIMIDAZOLES - A 1,3-DIPOLAR CYCLOADDITION ROUTE TO PYRROLO[1,2-A]IMIDAZOLES, PYRROLIDINES AND PYRROLES

Authors
JONES RCF HOWARD KJ NICHOLS JR SNAITH JS
Citation
Rcf. Jones et al., ANNULATION OF DIHYDROIMIDAZOLES - A 1,3-DIPOLAR CYCLOADDITION ROUTE TO PYRROLO[1,2-A]IMIDAZOLES, PYRROLIDINES AND PYRROLES, Journal of the Chemical Society. Perkin transactions. I (Print), (13), 1998, pp. 2061-2072
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I (Print) → ACNP
ISSN journal
0300922X
Issue
13
Year of publication
1998
Pages
2061 - 2072
Database
ISI
SICI code
0300-922X(1998):13<2061:AOD-A1>2.0.ZU;2-7
Abstract
4,5-Dihydroimidazolium ylides, formed by N-alkylation of 4,5-dihydroim idazoles, undergo diastereoselective endo 1,3-dipolar cycloaddition wi th electron-deficient alkene dipolarophiles to afford hexahydropyrrolo [1,2-a]imidazoles; reduction of the aminal functionality in the cycloa dducts leads to substituted pyrrolidines, Cycloaddition using 2-chloro propenonitrile, followed by base treatment, affords pyrroles.