Catalytic formal [4 + 1] isocyanide-based cycloaddition: an efficient strategy for the synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives
An unprecedented catalytic isocyanide-based cycloaddition of alkyl and aryl isocyanides with (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes was developed for the direct and efficient synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives. On the basis of DFT calculations, a mechanism is pr...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2019
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| In: |
Organic & biomolecular chemistry
Year: 2018, Volume: 17, Issue: 2, Pages: 275-282 |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/C8OB02857E |
| Online Access: | Verlag, Volltext: https://doi.org/10.1039/C8OB02857E Verlag, Volltext: https://pubs.rsc.org/en/content/articlelanding/2019/ob/c8ob02857e 
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| Author Notes: | Milad Motaghi, Hormoz Khosravi, Saeed Balalaie and Frank Rominger |
| Summary: | An unprecedented catalytic isocyanide-based cycloaddition of alkyl and aryl isocyanides with (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes was developed for the direct and efficient synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives. On the basis of DFT calculations, a mechanism is proposed involving formal [4 + 1] cycloaddition of isocyanides, followed by imine-enamine tautomerization and air oxidation. |
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| Item Description: | First published on 05 Dec 2018 Gesehen am 01.04.2019 |
| Physical Description: | Online Resource |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/C8OB02857E |