Chemical Science, Journal Year: 2024, Volume and Issue: 15(37), P. 15205 - 15211
Published: Jan. 1, 2024
The targeted and selective replacement of a single atom in an aromatic system represents powerful strategy for the rapid interconversion molecular scaffolds. Herein, we report pyridine-to-benzene transformation
Language: Английский
Nature, Journal Year: 2023, Volume and Issue: 618(7963), P. 21 - 24
Published: May 31, 2023
Language: Английский
Citations
49
Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(3), P. 242 - 251
Published: Jan. 9, 2024
Language: Английский
Citations
37
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(4), P. 2845 - 2854
Published: Jan. 18, 2024
In this report, we developed a unified and standardized one-pot sequence that converts pyridine derivatives into 1,2-diazepines by inserting nitrogen atom. This skeletal transformation capitalizes on the in situ generation of 1-aminopyridinium ylides, which rearrange under UV light irradiation. A thorough evaluation key parameters (wavelength, reaction conditions, activating agent) allowed us to elaborate simple, mild, user-friendly protocol. The model was extrapolated more than 40 examples, including drug derivatives, affording unique 7-membered structures. Mechanistic evidence supports transient presence diazanorcaradiene species. Finally, pertinent transformations products, ring contraction reactions form pyrazoles, were conducted paved way broad application
Language: Английский
Citations
34
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(5), P. 2939 - 2943
Published: Jan. 12, 2024
A practical method for the synthesis of 15N-labeled azines with a high degree isotopic enrichment is described. Activation azine heterocycles an electron-deficient arene allows facile substitution nitrogen atom specifically designed reagent that undergoes canonical ANRORC-type mechanism. wide range can be converted to their corresponding 15N isotopologs using this method, and it also dearomative access reduced heterocyclic congeners. short formal 15N-solifenacin accomplished as well demonstrate application generating labeled pharmaceuticals.
Language: Английский
Citations
26
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(32), P. 17570 - 17576
Published: Aug. 3, 2023
In this study, we describe the direct insertion of an intramolecular nitrogen atom into aromatic C–C bond. transformation, carbamoyl azides are activated by a Rh catalyst and subsequently directly inserted bond arene ring to access fused azepine products. This transformation is challenging, owing existence competitive C–H amination pathway. The use paddlewheel dirhodium complex Rh2(esp)2 effectively inhibited undesired insertion. Density functional theory calculations were performed reveal reaction mechanism origin chemoselectivity Rh-catalyzed reactions. novel products highly robust allow for downstream diversification.
Language: Английский
Citations
33
Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(7), P. 1975 - 1981
Published: May 11, 2023
Language: Английский
Citations
29
Acta Pharmaceutica Sinica B, Journal Year: 2023, Volume and Issue: 14(3), P. 1030 - 1076
Published: Nov. 18, 2023
Synthetic chemistry plays an indispensable role in drug discovery, contributing to hit compounds identification, lead optimization, candidate drugs preparation, and so on. As Nobel Prize laureate James Black emphasized, "the most fruitful basis for the discovery of a new is start with old drug"
Language: Английский
Citations
25
Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)
Published: Aug. 29, 2023
Classical metalation reactions such as the metal-halogen exchange have had a transformative impact on organic synthesis owing to their broad applicability in building carbon-carbon bonds from carbon-halogen bonds. Extending logic metal-carbon would enable direct modification of carbon frameworks with new implications retrosynthetic analysis. However, transformation requires selective cleavage highly inert chemical and formation stable intermediates amenable further synthetic elaborations, hence its development has remained considerably challenging. Here we introduce skeletal strategy that allows lactams, prevalent motif bioactive molecules, be readily converted into well-defined, synthetically useful organonickel reagents. The reaction features activation unstrained amide C-N mediated by an easily prepared Ni(0) reagent, followed CO deinsertion dissociation under mild room temperature conditions formal carbonyl-to-nickel-exchange process. underlying principles this unique reactivity are rationalized organometallic computational studies. is applied excision isotope underscoring potential synthesis.
Language: Английский
Citations
24
Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8419 - 8423
Published: Nov. 20, 2023
Recent advances in single-atom insertion reactions have opened up new synthetic approaches for molecular diversification. Developing innovative strategies to directly transform biologically relevant molecules, without any prefunctionalization, is key further expanding the scope and utility of such transformations. Herein, direct access quinazolines pyrimidines from corresponding unprotected 1H-indoles 1H-pyrroles reported, relying on implementation lithium bis(trimethylsilyl)amide (LiHMDS) as a novel nitrogen atom source combination with commercially available hypervalent iodine reagents. Further application this strategy late-stage settings demonstrates its potential lead structure diversification campaigns.
Language: Английский
Citations
23
Chemical Science, Journal Year: 2024, Volume and Issue: 15(7), P. 2612 - 2617
Published: Jan. 1, 2024
Advances in site-selective molecular editing have enabled structural modification on complex molecules.
Language: Английский
Citations
14