Cascade [3 + 2]/[4 + 2] Cycloaddition of Enaminones with Vinylene Carbonate for the Synthesis of Functionalized Pyrrolo[2,1-a]isoquinoline Derivatives DOI
Jianbo Ma,

Qing-Sheng Zhao,

Yiyong Yin

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9752 - 9758

Published: Nov. 6, 2024

We developed a protocol for the synthesis of functionalized pyrrolo[2,1-a]isoquinoline derivatives (PIQDs) 3 from enaminones 1 using vinylene carbonate 2. This strategy involved [3 + 2] and [4 cycloadditions via heating mixture substrates with 2 DCE at 60 °C, catalyzed by [Cp*RhCl2]2 oxidized Cu(OAc)2 AgSbF6 promoted NaOAc. As we increased reaction temperature to 110 °C under same conditions, synthesized PIQDs 4 through sequential C–H activation, alkene insertion, migratory C–N reductive elimination, β-O finally dehydration. result, series 3–4 were generated forming four bonds (2 C–C bonds) in single step. realizes linear molecules potential biological activity, specifically natural-like heterocycles (3–4). It expands application as C2 synthon construction pyrrole isoquinoline skeletons combinatorial parallel syntheses one-pot reactions.

Language: Английский

Cascade [3 + 2]/[4 + 2] Cycloaddition of Enaminones with Vinylene Carbonate for the Synthesis of Functionalized Pyrrolo[2,1-a]isoquinoline Derivatives DOI
Jianbo Ma,

Qing-Sheng Zhao,

Yiyong Yin

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9752 - 9758

Published: Nov. 6, 2024

We developed a protocol for the synthesis of functionalized pyrrolo[2,1-a]isoquinoline derivatives (PIQDs) 3 from enaminones 1 using vinylene carbonate 2. This strategy involved [3 + 2] and [4 cycloadditions via heating mixture substrates with 2 DCE at 60 °C, catalyzed by [Cp*RhCl2]2 oxidized Cu(OAc)2 AgSbF6 promoted NaOAc. As we increased reaction temperature to 110 °C under same conditions, synthesized PIQDs 4 through sequential C–H activation, alkene insertion, migratory C–N reductive elimination, β-O finally dehydration. result, series 3–4 were generated forming four bonds (2 C–C bonds) in single step. realizes linear molecules potential biological activity, specifically natural-like heterocycles (3–4). It expands application as C2 synthon construction pyrrole isoquinoline skeletons combinatorial parallel syntheses one-pot reactions.

Language: Английский

Citations

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