Shaking Up the Friedländer Reaction: Rapid, Scalable Mechanochemical Synthesis of Polyaryl‐Substituted Quinolines
Why this work is in the frame
A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.
Bibliographic record
Abstract
Abstract Quinolines are ubiquitous heterocyclic aromatic scaffolds, which can be found in many natural and synthetic products. They are highly valued for their pharmacological and electrochemical properties, encouraging the discovery of new routes for quinoline synthesis and diversification. In particular, polyaryl‐substituted quinolines have recently surged as useful substrates for a wide variety of applications, yet their synthetic routes remain difficult and inefficient. Herein, we report a rapid and novel mechanochemical Friedländer synthesis of polyaryl‐substituted quinolines under basic conditions using ball milling. The optimized reaction conditions resulted in moderate to excellent yields ranging from 48% to >95% and demonstrated broad functional group tolerance at 1 hour reaction times. We further show a new route for the synthesis of photocatalyst DPQN 2,4−di−OMe and photo‐ligand PPQN 2,4−di−OMe as well as OLED donor‐acceptor pCzPPQ, electron transport material oligoquinoline TQB and organic semiconductor DPA. A gram scale reaction was also achieved using Resonant Acoustic Mixing (RAM), providing an isolated yield of 87% after a simple recrystallization in ethanol.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
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) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 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