One-Pot Synthesis of 2-Acetyl-1 H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

Date

2021-01-01

Author

Kanova, Nilay
Dündar, Buse Ayşen
Kelgokmen, Yilmaz
Zora, Metin

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A one-pot two-step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic β-enaminones was described. When treated with zinc chloride in refluxing chloroform, N-propargylic β-enaminones produced in situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further refluxing in methanol with zinc chloride, afforded 2-acetyl-1H-pyrroles. The process was found to be general for a wide variety of N-propargylic β-enaminones and yielded a diverse range of 2-acetyl-1H-pyrroles in good to high yields with large substrate scope and good functional group tolerance. This operationally easy method may provide a rapid access to functionalized 2-acetyl-1H-pyrroles of pharmacological interest.

URI

https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85105082854&origin=inward
https://hdl.handle.net/11511/90888

Journal

Journal of Organic Chemistry

DOI

https://doi.org/10.1021/acs.joc.1c00077

Collections

Department of Chemistry, Article

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Citation Formats

N. Kanova, B. A. Dündar, Y. Kelgokmen, and M. Zora, “One-Pot Synthesis of 2-Acetyl-1 H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines,” Journal of Organic Chemistry, pp. 0–0, 2021, Accessed: 00, 2021. [Online]. Available: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85105082854&origin=inward.