In this study, a Rh(III)-catalyzed C-H/N-H [4+2] annulation of oxadiazolones with iodonium ylides has been developed, which afforded a series of diverse fused-isoquinolines and fused-pyridines in moderate to high yields. These divergent synthesis protocols featured mild conditions, broad substrate scope, and functional-group compatibility. In addition, scale-up synthesis, related applications and preliminary mechanistic explorations were also accomplished.
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http://dx.doi.org/10.1039/d4cc02046d | DOI Listing |
Chem Commun (Camb)
December 2024
School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China.
A Rh(III)-catalyzed C-H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones was realized, which afforded various -fluoroalkenylation β-ketosulfoxonium ylides with high -selectivity and diverse oxadiazolone fused-isoquinolines. This protocol featured mild conditions, broad substrate scope, and functional-group compatibility. In addition, scale-up synthesis, related applications and preliminary mechanistic explorations were also accomplished.
View Article and Find Full Text PDFJ Org Chem
November 2024
Fraunhofer Institute for Translational Medicine and Pharmacology ITMP, Theodor-Stern-Kai 7, 60596 Frankfurt am Main, Germany.
Nitrogen-containing heterocycles are present in most approved drugs, reflecting the significance of their synthetic strategies. By utilizing oxadiazolone as a nitrenoid (nitrene-like) precursor, we have developed a general strategy for the annulation with nucleophilic heterocycles to access various polycyclic aminoheterocycles. We have discovered that 2-pyrryl-substituted substrates undergo a rearrangement, which indicates a spirocyclization-migration pathway.
View Article and Find Full Text PDFChem Commun (Camb)
June 2024
School of Pharmacy, Guangdong Provincial Key Laboratory of Advanced Drug Delivery, Guangdong Provincial Engineering Center of Topical Precise Drug Delivery System, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China.
In this study, a Rh(III)-catalyzed C-H/N-H [4+2] annulation of oxadiazolones with iodonium ylides has been developed, which afforded a series of diverse fused-isoquinolines and fused-pyridines in moderate to high yields. These divergent synthesis protocols featured mild conditions, broad substrate scope, and functional-group compatibility. In addition, scale-up synthesis, related applications and preliminary mechanistic explorations were also accomplished.
View Article and Find Full Text PDFOrg Lett
May 2023
School of Pharmaceutical Science and Technology, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China.
A Rh(III)-catalyzed C-H bond activation for the synthesis of fused 2-isoindole scaffolds from oxadiazolones with diazo compounds was developed. The reaction proceeded through C-H activation of oxadiazolones/[4 + 1] annulation, intramolecular cyclization, and an unusual acyl migration cascade to afford target scaffolds with good yields. These 2-isoindole derivatives could be further transformed into intriguing drug privileged scaffolds.
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