A Synthon for the Convenient and Efficient Introduction of Tetrazolylmethyl Groups into Nucleophile‐Bearing Compounds
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Bibliographic record
Abstract
Abstract An activated synthon for the efficient introduction of a protected tetrazolylmethyl group into nucleophile‐bearing compounds is presented. The β‐cyanoethyl protecting group allows for very effective deprotection under mild basic conditions. The synthon can be prepared by a two‐step procedure (42 %) starting from cheap starting material and can alkylate piperidine in 91 % yield. Even quadruple alkylation to form a protected version of the hexadentate ligand EDTT gives decent yields. Simultaneous removal of the four protecting groups furnishes the lithium salt of a formally zwitterionic ligand in 75 % yield. Finally, the synthon's performance has been assessed by comparison with its benzyl‐protected counterpart and was found to be equally efficient in the alkylation of simple amines but superior in deprotection. For substrates bearing basic amine sites, the β‐cyanoethyl group is largely preferable.
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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 | 0.001 | 0.001 |
| 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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 it