Sequential base-promoted formal (4+2) allenoate based cycloaddition: synthesis of functionalized acridines
Base-promoted formal [4+2] cycloaddition reaction of (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes and allenoates represents an efficient method for the synthesis of functionalized acridines through a sequential Michael addition, aldol condensation, and isomerization process in a mild cond...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
[September 13, 2022]
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| In: |
European journal of organic chemistry
Year: 2022, Issue: 34, Pages: 1-5 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.202200830 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.202200830 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202200830 
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| Author Notes: | Toktam S. Shirazian, Hossein Zahedian Tejeneki, Ali Nikbakht, Frank Rominger, and Saeed Balalaie |
| Summary: | Base-promoted formal [4+2] cycloaddition reaction of (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes and allenoates represents an efficient method for the synthesis of functionalized acridines through a sequential Michael addition, aldol condensation, and isomerization process in a mild condition. This new approach tolerates a wide range of (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes and allenoates and affords the functionalized acridines in good to excellent yields. The exclusive selectivity, high atom economy, and high bond-formation efficiency of this method makes it a valuable approach for the synthesis of acridine backbones. |
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| Item Description: | Gesehen am 24.10.2022 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.202200830 |