A robust route to 2,4-disubstituted pyrrole heterocycles relying upon a cascade reaction is reported. The reaction benefits from operational simplicity: it is air and moisture tolerant and is performed at ambient temperature. Control over the reaction conditions provides ready access to isopyrroles, 2,3,4-trisubstituted pyrroles, and 3-substituted pyrollidin-2-ones.
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http://dx.doi.org/10.1021/ja110117g | DOI Listing |
Herein, we present a sustainable and atom-economical approach for the synthesis of quinazolinones via acceptorless dehydrogenative coupling (ADC) using earth-abundant Co-salt, (CoCl2) as the catalyst under neat condition. This method is distinguished by its green credentials, like, solvent-free, microwave-assisted heating, cost-effective, use of renewable alcohols, and generating only H2 and water as byproducts. Remarkably, this protocol achieves quinazolinone synthesis without the need for external ligands, oxidants, or additional additives.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Pharmacy, College of Pharmacy, Kyung Hee University, 26 Kyungheedae-ro, Dongdaemun-gu, Seoul 02447, Republic of Korea.
In this study, we developed palladium-catalyzed dehydrogenative cyclization to transform 1-(2-aminoaryl)-3-arylpropan-1-ones into 2-arylquinolin-4(1)-ones, also known as aza-flavones which are the bioisosteres of flavones, in an atom-economic manner. This method exhibited excellent chemical compatibility with a broad substrate scope, accommodating up to 25 derivatives. Additionally, kinetic studies were performed to elucidate the reaction mechanism.
View Article and Find Full Text PDFChemistry
January 2025
Department of Chemistry, Indian Institute of Technology Kharagpur Kharagpur 721302, West Bengal, India.
All-carbon quaternary and tertiary stereocenters connected at the C2-position of functionalizable C3-alkylated indole nucleus are commonly occurring frameworks found in many indole alkaloids of medicinal importance. Their direct access is scarcely reported, a long-standing problem, and developing a unique yet simple method can pave the pathway to an entirely different retrosynthetic route for the total synthesis of these alkaloids. Herein, this problem is addressed by developing an unprecedented branch-selective allylation strategy employing a broad range of structurally and electronically different 3-alkenyl-indoles and allylboronic acids.
View Article and Find Full Text PDFJ Org Chem
January 2025
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 PDFSmall
December 2024
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.
A mixed-ligand-based thermo-chemically robust and undulated metal-organic framework (MOF) is developed that embraces carboxamide moiety-grafted porous channels and activation-induced generation of open-metal site (OMS). The guest-free MOF acts as an outstanding heterogeneous catalyst in Hantzsch condensation for electronically assorted substrates with low catalyst loading and short duration under greener conditions than the reported materials. Besides Lewis acidic OMS, the carboxamide group activates the substrate via two-point hydrogen bonding, highlighting the effectiveness of custom-made functionalities in this multi-component reaction.
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