Synthesis of Indolizines by Dimerization of N-Propargylated Pyrroles Via Allene Intermediates
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Date
2021
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley-v C H verlag Gmbh
Abstract
Ten different N-propargyl pyrrole derivatives having various substituents at the C-2 position were synthesized. These derivatives were converted into indolizine derivatives by the [2+2] cycloaddition reaction of pyrrole N-allene, forming in situ, by heating in PrOH in basic medium. The structures were characterized by NMR and X-ray crystallography. The N-propargylated derivatives smoothly underwent intermolecular cyclizations to produce indolizine derivatives in good yields. We proposed a radical mechanism for the dimerization. Reaction of an allene product with butylated hydroxytoluene (BHT), a radical scavenger, did not give any dimerization product. This result supports the radical reaction.
Description
Menges, Nurettin/0000-0002-5990-6275
ORCID
Keywords
Allene, Indolizine, Intermolecular Cyclization, Radical Reaction, Radical Scavenger
Turkish CoHE Thesis Center URL
WoS Q
Q3
Scopus Q
Q3
Source
Volume
6
Issue
9
Start Page
2366
End Page
2372