A new guanidinylation procedure for the preparation of functionalized guanidines and investigation towards the synthesis of cyclic quanidine compounds
Why this work is in the frame
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Bibliographic record
Abstract
This thesis is a summary of research conducted since October 2000 at the University of Toronto in the laboratory of Dr. Robert A. Batey. This manuscript is divided into three chapters. Chapter one provides a brief introduction to the guanidine functional group and guanidine-containing compounds, both natural and synthetic. Chapter two describes a new method for alkylation of guanidine-containing compounds using a convenient and mild biphasic protocol. This approach requires limited purification of the obtained products, yielding highly functionalized guanidines in good to excellent yields. This protocol has been used with a variety of alkyl halides and mesylates and provides an alternate approach to methods currently utilized in the literature. Chapter three describes investigations towards the synthesis of cyclic guanidine compounds. Initially, iodocyclization reactions were attempted; however, limited success was encountered with this approach. Palladium-catalyzed π-allyl chemistry was then investigated to synthesize the cyclic guanidine compounds. Thus far, investigations with this approach have been successful and a general approach for the synthesis of cyclic guanidine compounds using palladium π-allyl chemistry is described for the first time within our labs.
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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 | 0.004 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.001 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.001 | 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