Divergent Reactivity of <i>N</i>-Isocyanates with Primary and Secondary Amines: Access to Pyridazinones and Triazinones
Why this work is in the frame
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Bibliographic record
Abstract
Cascade reactions for the synthesis of 1,2,4-triazinones and 5-aminopyridazinones are reported using α-ketocarbazones as N-isocyanate precursors and exploiting the divergent reactivity observed with primary and secondary amines. Triazinones were formed with primary amines, likely through addition of the amine on the N-isocyanate, followed by cyclization (condensation) on the ketone. In contrast, such cyclization is impossible for secondary amines; this allows in situ formation of enamines, which, upon cyclization, generate 5-amino pyridazinones. This sequence further illustrates the versatility of N-isocyanates in heterocyclic synthesis and provides a rare example of carbon nucleophiles reacting with N-isocyanates.
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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 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| 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) | 0.000 | 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 it