Cascade C=O/C=C/C-N bond formation: metal-free reactions of 1,4-diynes and 1-En-4-yn-3-ones with isoquinoline and quinoline N-oxides
The metal-free reactions of 1,4-diynes and 1-en-4-yn-3-ones with isoquinoline and quinoline N-oxides are developed, resulting in the formation of 3,4-dihydro-2H-pyrido[2,1-a]isoquinolines and 2,3-dihydro-1H-pyrido[1,2-a]quinolines via cascade C═O/C═C/C-N bond formation. It is the first report in whi...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
July 28, 2017
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| In: |
Organic letters
Year: 2017, Volume: 19, Issue: 16, Pages: 4327-4330 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.7b01996 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1021/acs.orglett.7b01996 Verlag, Volltext: http://pubs.acs.org/doi/abs/10.1021%2Facs.orglett.7b01996 Verlag, Volltext: http://pubs.acs.org/doi/pdf/10.1021/acs.orglett.7b01996 
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| Author Notes: | Bing Zhang, Long Huang, Shiwei Yin, Xuetong Li, Tao Xu, Biyang Zhuang, Tao Wang, Zunting Zhang, A. Stephen K. Hashmi |
| Summary: | The metal-free reactions of 1,4-diynes and 1-en-4-yn-3-ones with isoquinoline and quinoline N-oxides are developed, resulting in the formation of 3,4-dihydro-2H-pyrido[2,1-a]isoquinolines and 2,3-dihydro-1H-pyrido[1,2-a]quinolines via cascade C═O/C═C/C-N bond formation. It is the first report in which in the alkyne oxidation by N-oxides both the oxygen atom of N-oxides and the nitrogen atom are involved in a second C-heteroatom bond formation. The reactions showed a broad substrate scope and functional group tolerance. Furthermore, the products were found to display green-blue fluorescence in DMSO with fluorescence quantum yields up to 0.59. |
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| Item Description: | Gesehen am 23.11.2017 |
| Physical Description: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.7b01996 |