Synthesis of Indolizines by Dimerization of N-Propargylated Pyrroles via Allene Intermediates

Date

2021-03-01

Author

Kuzu, Burak
Gul, Sergen
Tan Uygun, Meltem
Mengeş, Nurettin
Balcı, Metin

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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.

URI

https://hdl.handle.net/11511/89755

Journal

CHEMISTRYSELECT

DOI

https://doi.org/10.1002/slct.202100045

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Graduate School of Natural and Applied Sciences, Article

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Citation Formats

B. Kuzu, S. Gul, M. Tan Uygun, N. Mengeş, and M. Balcı, “Synthesis of Indolizines by Dimerization of N-Propargylated Pyrroles via Allene Intermediates,” CHEMISTRYSELECT, pp. 2366–2372, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/89755.