Synthesis of 1-Azaspiro[4.5]deca-1,3-dienes from N-Propargylic beta-Enaminones in Basic Medium

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2019-05-01

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KARADENİZ, EDA
Zora, Metin

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A facile, efficient and unprecedented method for the synthesis of spiro-2H-pyrroles is reported. When reacted with 1-ethynylcyclohexylamine, a, ss-alkynic ketones produced cyclohexane-embedded Npropargylic ss-enaminones, which in the presence of cesium carbonate underwent nucleophilic cyclization to afford 1-azaspiro[ 4.5] deca-1,3diene derivatives in good to excellent yields. This cyclization was found to be general for a variety of cyclohexane-embedded N-propargylic ss enaminones and demonstrated good tolerance to a broad range of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The decoration of pyrrole compounds with a spiro framework may exhibit potential for the synthesis of molecules of pharmacological interest.

Subject Keywords

Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/45849

Journal

SYNTHESIS-STUTTGART

DOI

https://doi.org/10.1055/s-0037-1611723

Collections

Department of Chemistry, Article

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Citation Formats

E. KARADENİZ and M. Zora, “Synthesis of 1-Azaspiro[4.5]deca-1,3-dienes from N-Propargylic beta-Enaminones in Basic Medium,” SYNTHESIS-STUTTGART, pp. 2157–2170, 2019, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/45849.