Indium-catalyzed formal (4 + 1 + 1)/(4 + 1) isocyanide-based annulation for construction of polyfunctionalized pyrano- and furoquinolines
A distinctive catalytic reaction involving multiple isocyanide insertions on ambiphilic quinolines has been introduced to synthesize intricate polyheterocyclic scaffolds (21 examples, up to 71% yield) through the formation of several C-C, C-O, and C-N bonds. Our findings indicate that these reaction...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
9 May 2025
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| In: |
Organic & biomolecular chemistry
Year: 2025, Volume: 23, Issue: 22, Pages: 5423-5427 |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/D5OB00512D |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1039/D5OB00512D Verlag, kostenfrei, Volltext: https://pubs.rsc.org/en/content/articlelanding/2025/ob/d5ob00512d 
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| Author Notes: | Issa Zarei, Hormoz Khosravi, Frank Rominger, Leila Rezaei Somee and Saeed Balalaie |
| Summary: | A distinctive catalytic reaction involving multiple isocyanide insertions on ambiphilic quinolines has been introduced to synthesize intricate polyheterocyclic scaffolds (21 examples, up to 71% yield) through the formation of several C-C, C-O, and C-N bonds. Our findings indicate that these reactions can switch between two cycloadditions ([4 + 1 + 1] and [4 + 1]) depending on the isocyanide structure and the solvent used. Finally, furo[2,3-b]quinoline-2,3-diamine examples, as some of the novel products, exhibit strong solvatochromism in various solvents. |
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| Item Description: | Im Titel steht der Ausdruck [4 + 1 + 1]/[4 + 1] in eckigen Klammern Gesehen am 27.10.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/D5OB00512D |