Verdazyl Radicals as Substrates for Organic Synthesis: Unique Access to Tetrahydropyrazolotriazinones, Pyrazolotriazinones and Dihydrotetrazinylacrylonitriles
Bibliographic record
Abstract
Abstract 1,5‐Dimethyl‐3‐phenyl‐6‐oxoverdazyl radical was recently shown to undergo a disproportionation reaction to form an azomethine imine, which reacted with a series of dipolarophiles, to form novel tetrahydropyrazolotetrazinone heterocyclic structures, demonstrating for the first time the use of verdazyl radicals as substrates for organic synthesis. Herein, we report on the chemistry of this verdazyl radical with captodative olefins and show that the reactions that occur, either an addition reaction or a hydrogen abstraction reaction followed by a cycloaddition reaction, are defined by the captodative olefin. Also highlighted is an intramolecular rearrangement of initially formed tetrahydropyrazolotetrazinone cycloadducts to either pyrazolotriazinone or tetrahydropyrazolotriazinone structures. While the rearrangement falls under the very general definition of the Dimroth rearrangement, the mechanism that is proposed is distinct and provides the opportunity to go from one particular structural motif to another under mild conditions, expanding the usefulness of this chemistry.
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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 | 0.001 | 0.008 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.002 | 0.000 |
| Research integrity | 0.000 | 0.002 |
| Insufficient payload (model declined to judge) | 0.006 | 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".