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Palladium(II)-catalyzed cyclization of heterocyclic ketene aminals with (E)-ethyl 2,3-diiodoacrylates: selective synthesis of bicyclic pyrroles and bicyclic pyridones.
- Source :
-
Tetrahedron . Jul2014, Vol. 70 Issue 30, p4478-4484. 7p. - Publication Year :
- 2014
-
Abstract
- Abstract: A concise and efficient synthesis of novel bicyclic pyrroles has been achieved by PdCl2-catalyzed cyclic condensation of six-membered heterocyclic ketene aminals (HKAs) or seven-membered HKAs with ethyl 2,3-diiodoacrylate and diethyl 2,3-diiodofumarate in the presence of Cs2CO3, respectively. A series of novel bicyclic pyridones have also been obtained via five-membered HKAs with diethyl 2,3-diiodofumarate under the optimized conditions in moderate yields. These reactions are the first application of a transition metal to catalyze the building blocks HKAs to form the bicyclic pyrrole library via condensation reaction. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 70
- Issue :
- 30
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 96231770
- Full Text :
- https://doi.org/10.1016/j.tet.2014.05.032