Quinolines and its derivatives are significant class of heterocyclic compounds which are identified as the key component in many natural products and biologically important molecules. We describe herein a facile method for the synthesis of quinoline derivatives from Morita-Baylis-Hillman (MBH) Alcohols Palladium Catalyzed intramolecular aryl amination followed by allylic amination pathway. The reaction between a series of MBH alcohols and amino compounds (Tosyl, aliphatic and aromatic amines) under optimized reaction conditions with Pd(PPh)Cl/DPPP catalyst system, afforded the corresponding 1,2-dihydroquinolines upto 95 % isolated yield.
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http://dx.doi.org/10.1002/slct.202003413 | DOI Listing |
Org Lett
December 2024
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. China.
A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Indian Institute of Science Education and Research (IISER)-Pune, Dr. Homi Bhabha Road, Pashan, Pune, Maharashtra 411008, India.
A Pd (II)-catalyzed direct C3-(sp)-H alkenylation of heteroarenes using benzothiazole as a directing group was successfully achieved. A wide range of 2--alkylpyrroles undergo an oxidative coupling with a variety of acrylates to furnish highly regio- and chemoselective E-alkenylation products at the C3 position. An important intermediate complex has been isolated and characterized so as to have an insight into the mechanism.
View Article and Find Full Text PDFJ Org Chem
December 2024
Jiangsu Key Laboratory for Chemistry of Low Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, China.
An unprecedented Pd-catalyzed cascade alkyne insertion/Heck/C-H activation reaction of -iodophenyl alkenyl ethers and diarylacetylenes has been developed. Diversified tetracyclic-fused dihydroindeno[2,1-]chromenes bearing a quaternary center were constructed in an efficient, straightforward, and atom-economic way with good to excellent yields. The protocol features high bonding efficiency, operational simplicity, broad substrate scope, and easy scale-up.
View Article and Find Full Text PDFJ Org Chem
December 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China.
A palladium-catalyzed asymmetric chlorocyclization of 1,6-enynes has been described. Controlling the chloride ion concentration in the system by substrate design is the key to achieving asymmetric chlorinated cyclization. In the presence of Pd(PhCN)Cl and chiral phosphoramidite ligands, the reaction accesses diverse chiral ()-α-chloromethylene-γ-butyrolactams with excellent selectivity and enantioselectivity.
View Article and Find Full Text PDFOrg Lett
December 2024
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi 502 284, Sangareddy District, Telangana, India.
This study demonstrates quick access to heteroatom-embodied complex fused polycyclic frameworks through a palladium-catalyzed domino process facilitated by microwave-assisted crossover annulation of -alkynylarylhalides and dihydrobenzofurans derivatives. The overall success of this process lies in the careful design of dihydrobenzofuran precursors that direct the initial palladium-mediated annulation step to proceed in a highly regioselective manner to furnish a single regioisomeric product. Notably, this one-pot method has witnessed good substrate scope and has furnished products with excellent yields.
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