Ring-Opening Reconstruction of Indoles Enabled by C–N Bond Cleavage: Synthesis of Benzo[ <i>c</i> ]pyrazolo[3,4- <i>h</i> ][2,6]naphthyridine Derivatives
Bibliographic record
Abstract
Here we report the iodine-mediated tandem process of indole-ring-opening reconstruction, which accomplishes scaffold hopping from indoles to polycyclic heteroaromatics (PHAs), offering the advantages of simple operation and easily accessible substrates. The proposal is compatible with a wide range of active molecules and natural products, affording derivatives endowed with both thermally activated delayed fluorescence (TADF) and aggregation-induced emission (AIE) properties. Importantly, the reaction mechanism was further investigated by density functional theory (DFT) calculations, confirming that the reaction involves chemoselective formation of a diene and a stereoselective [4 + 2] cycloaddition. The analyses further clarify that a hindering group at the 2-position of the indole is critical for driving the C-N bond ring-opening and recombination process. This work highlights the versatility of the approach as a strategic extension to advancing indole chemistry and skeletal reconstruction.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".