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Synthesis of 1-Azaspiro[4.5]deca-1,3-dienes from N-Propargylic β-Enaminones in Basic Medium
| Content Provider | Semantic Scholar |
|---|---|
| Author | Karadeniz, Eda Zora, Metin |
| Copyright Year | 2019 |
| Abstract | A facile, efficient and unprecedented method for the synthesis of spiro-2H-pyrroles is reported. When reacted with 1-ethynylcyclohexylamine, α,β-alkynic ketones produced cyclohexane-embedded N-propargylic β-enaminones, which in the presence of cesium carbonate underwent nucleophilic cyclization to afford 1-azaspiro[4.5]deca-1,3-diene derivatives in good to excellent yields. This cyclization was found to be general for a variety of cyclohexane-embedded N-propargylic β-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. |
| Starting Page | 2157 |
| Ending Page | 2170 |
| Page Count | 14 |
| File Format | PDF HTM / HTML |
| DOI | 10.1055/s-0037-1611723 |
| Alternate Webpage(s) | https://www.thieme-connect.com/media/synthesis/EFirst/supmat/sup_ss-2018-t0789-op_10-1055_s-0037-1611723.pdf |
| Alternate Webpage(s) | https://doi.org/10.1055/s-0037-1611723 |
| Volume Number | 51 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |