173549-48-9Relevant articles and documents
On the Preparation of N-Acylpyrroles and their Use in the Synthesis of Ketones
Brandaenge, Svante,Holmgren, Erik,Leijonmarck, Hans,Rodriguez, Benito
, p. 922 - 928 (2007/10/03)
Two methods for the preparation of N-acylpyrroles have been studied: (a) the reaction between pyrrole and N-acylimidazoles and (b) the oxidation of amides of 3-pyrroline.The reactions between N-acylpyrroles and organolithium compounds can be directed to give ketones in good yields.The initially formed tetrahedral intermediates in these reactions are relatively stable and pyrrolylcarbinols are isolable intermediates.A Reformatsky-Claisen type ring-closure gave a more than doubled yield when an N-acylpyrrole group was used as an electrophile instead of an ester group; the increased stability of the initially formed tetrahedral intermediate presumably accounts for the observed results.
