AI Article Synopsis
- Di(het)aryldiynes react with -benzylaldimines through a [4 + 3] cycloaddition using the KOBu/DMSO system, leading to tetra(het)arylsubstituted 3-azepines with yields up to 71%.
- The reaction involves adding azaallyl anions to the diynes, resulting in prototropic isomerization and subsequent cyclization with the other triple bond.
- This process is supported by quantum-chemical analysis, confirming the proposed mechanism.
Article Abstract
Di(het)aryldiynes smoothly react with -benzylaldimines in a [4 + 3] cycloaddition manner under the action of the KOBu/DMSO system (60 °C, 30 min) to afford pharmaceutically relevant tetra(het)arylsubstituted 3-azepines in up to 71% yield. The process involves the addition of azaallyl anions to one of the triple bonds of diynes followed by prototropic isomerization and cyclization of anionic intermediates with participation of the second triple bond. The cascade mechanism is consistent with quantum-chemical analysis (B2PLYP-D3/6-311+G**//B3LYP-D3/6-31+G* + PCM).
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| http://dx.doi.org/10.1021/acs.orglett.4c01531 | DOI Listing |
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