One-Pot Synthesis of Spiro-2H-pyrroles fromN-Propargylic beta-Enaminones

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2019-06-01

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KARADENİZ, EDA
Zora, Metin

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A simple and general one-pot method for the synthesis of spiro-2 H -pyrroles has been developed. Initially, cyclohexane-embedded -enaminones with internal alkyne functionality were synthesized by conjugate addition of 1-ethynylcyclohexylamine to ,-alkynic ketones, followed by palladium-catalyzed coupling of the resulting N -propargylic -enaminones with aryl iodides. When subjected to basic conditions, the cyclohexane-embedded -enaminones with internal alkyne functionality underwent tandem nucleophilic cyclization and benzylic C-H oxidation to furnish 3,4-diaryloyl-1-azaspiro[4.5]deca-1,3-diene derivatives in good yields.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/40822

Journal

SYNLETT

DOI

https://doi.org/10.1055/s-0037-1611816

Collections

Department of Chemistry, Article

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Citation Formats

E. KARADENİZ and M. Zora, “One-Pot Synthesis of Spiro-2H-pyrroles fromN-Propargylic beta-Enaminones,” SYNLETT, pp. 1231–1236, 2019, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40822.