Premium
A New Strategy for the Synthesis of 4‐Propargyl‐Substituted 1 H ‐Pyrroles from N ‐(5‐phenyl‐2,4‐pentadiynyl) β‐Enaminones
Author(s) -
Yilmaz Elif Serel,
Zora Metin
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902759
Subject(s) - propargyl , pyrrole , phenylacetylene , chemistry , dichloromethane , sodium hydride , alkyne , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , solvent
A new method for the synthesis of 4‐propargyl‐substituted 1 H ‐pyrroles is described. When treated with sodium hydride in refluxing dichloromethane, N ‐(5‐phenyl‐2,4‐pentadiynyl) β‐enaminones, synthesized by the coupling of N ‐propargylic β‐enaminones with phenylacetylene, afforded 4‐propargyl‐substituted pyrrole derivatives. This conversion was general for a variety of N ‐(5‐phenyl‐2,4‐pentadiynyl) β‐enaminones and displayed broad functional group tolerance. During the reaction, not only cyclization of linear precursors to pyrrole ring takes place, but also propargyl group is introduced to pyrrole core in one‐pot. The enrichment of pyrrole compounds with a propargyl unit might exhibit potential for the synthesis of heterocyclic molecules of pharmacological interest.