Direct <i>N</i>-Cyclopropylation of Cyclic Amides and Azoles Employing a Cyclopropylbismuth Reagent
Why this work is in the frame
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Bibliographic record
Abstract
Cyclopropanes are commonly found in medicinal chemistry since they provide unique spatial and electronic features, combined with high metabolic stability in liver microsomes. Although many methods are found in the chemist's arsenal to connect a cyclopropyl group to a carbon atom, none exist that perform the direct transfer of this useful fragment onto the nitrogen of a heterocycle or an amide. Considering the importance of nitrogenated compounds in the pharmaceutical industry, we sought to develop an expedient method to N -cyclopropylate azoles and amides. We report herein the direct cyclopropyl transfer reaction onto cyclic amides, isatins, oxindoles, imides, and carbamates employing a nonpyrophoric cyclopropylbismuth reagent. The reaction is catalyzed by copper acetate and proceeds smoothly in dichloromethane at 50 °C in the presence of pyridine. The N -cyclopropylation reaction can also be applied to the preparation of N -cyclopropyl indoles, benzimidazoles, pyrroles, and pyrazoles.
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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 | 0.001 |
| 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