Journal
SYNLETT
Volume 30, Issue 10, Pages 1231-1236Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611816
Keywords
pyrrole; 2H-pyrrole; N-propargylic beta-enaminones; spiro compound; nucleophilic cyclization; benzylic C-H oxidation
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Funding
- Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (Scientific and Technological Research Council of Turkey, TUBITAK) [114Z811]
- Orta Dogu Teknik Universitesi (Middle East Technical University, METU) [GAP-103-2018-2770]
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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.
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