Modular Synthesis of Substituted Lactams via a Deoxygenative Photochemical Alkylation–Cyclization Cascade of Secondary Amides in Flow
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Bibliographic record
Abstract
High Resolution Image Download MS PowerPoint Slide γ-Lactams are crucial scaffolds in many bioactive compounds and pharmaceutical agents, yet their synthesis featuring diverse γ- and N -substitution remains a significant synthetic challenge. Current methods often lack modularity and efficiency, particularly when targeting sterically hindered or highly functionalized analogues. Herein, we report a modular, three-step strategy for the systematic synthesis of γ- and N -substituted γ-lactams from readily available primary amines and carboxylic acids. The sequence includes deoxygenative activation of secondary amides using triflic anhydride, a photochemical silane-mediated radical alkylation, and intramolecular cyclization. The alkylation–lactamization cascade proceeds under additive-free, continuous-flow photochemical conditions, enabling rapid reaction times (20 min) and scalable operation. Compared to conventional N -alkylation approaches, this method broadens access to sterically hindered analogues and offers a valuable platform for medicinal chemistry applications.
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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 | 0.001 |
| 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 | 0.000 | 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 it