Research output: Contribution to journal › Article › peer-review
α-Diazopyrroles selectively react with enamines at room temperature to give either (4+2)-cycloaddition-dehydroamination cascade products, pyrrolo[2,1-c][1,2,4]triazines, or azo coupling products. The reaction was used for the synthesis of functionalized ortho-fused heterocycles with new tetrahydrobenzo[e]pyrrolo[2,1-c][1,2,4]triazine and tetrahydro-6H-cyclohepta[e]pyrrolo[2,1-c][1,2,4]triazine frameworks. Unstable azo compounds, 2-[(2-aminovinyl)diazenyl]pyrroles, were obtained from enamines of tetralone or acyclic ketones. According to the density functional theory calculations, (4+2)-cycloaddition of α-diazopyrroles with enamines proceeds in a nonconcerted manner via the zwitterionic intermediate, which undergoes cyclization to pyrrolotriazine or a competitive 1,5-prototropic shift leading to the formation of azo coupling product.
Original language | English |
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Pages (from-to) | 10485-10492 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 87 |
Issue number | 15 |
DOIs | |
State | Published - 5 Aug 2022 |
ID: 98529461