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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

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