Beilstein J. Org. Chem.2015,11, 228–232, doi:10.3762/bjoc.11.25
modified conditions of the Favorskyreaction has been implemented to pave an expedient route to important biomolecules containing a pyrrole ring.
Keywords: acetylene; ethynylation; Favorskyreaction; 1-vinylpyrrole-2-carbaldehyde; Introduction
Functionalized pyrroles bearing a terminal acetylenic moiety
, incapable of the above ionization, might normally undergo the Favorskyreaction. Indeed, this proves to be true.
This is a concise report on the first successful base-mediated ethynylation of 1-vinylpyrrole-2-carbaldehydes 1a–j with acetylene.
These N-substituted pyrrole-2-carbaldehydes have been chosen for
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Graphical Abstract
Scheme 1:
The reaction of pyrrole-2-carbaldehyde with acetylene.