An effective process for the green and rapid synthesis of biologically active polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazoles derivatives using Cu@imine/FeO MNPs catalyst under solvent-free conditions is explained. This catalyst showed high reactivity for the synthesis of a set of different derivatives of polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazole derivatives under appropriate reaction conditions and short times. Moreover, the catalyst was also recycled and reused for six runs with no considerable reduction in reactivity and yields. Compared to the reported procedures, this method consistently demonstrates the advantages of low catalyst loading, short reaction times, easy separation and purification of the products, high yields, and high recoverability and recoverability of the catalyst.
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http://dx.doi.org/10.1039/c9ra02325a | DOI Listing |
Chemistry
October 2024
Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Str.10, 91058, Erlangen, Germany.
We describe the synthesis and computational investigation of N-heterocycle-substituted hexa-peri-hexabenzocoronenes (HBCs). Following our method for the preparation of thioether-substituted HBCs, we prepared pyrrole-, indole-, carbazole-, and 1H-benz[g]indole-substituted HBCs from the corresponding fluorinated precursors under microwave irradiation. A series of polysubstituted benzoindole-HBCs with windmill architectures was also synthesized using the polyfluorinated HBC analogs, and the substituent effects on the electronic properties of the HBC core were investigated.
View Article and Find Full Text PDFOrg Lett
November 2024
Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay91400 Orsay, France.
A copper-catalyzed efficient, operationally simple, general method for straightforward syntheses of polysubstituted pyrroles employing ethynyl methylene cyclic carbamates as precursors reacting with commercially available amines was first reported. A wide variety of polysubstituted pyrroles were obtained in acceptable to good yields under mild conditions. This protocol features broad substrate scope, high functional group tolerance, and easy operation, therefore enabling late-stage functionalization and rapid synthesis of bioactive compounds, including structurally complex marketed drugs and natural products.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2024
Laboratory of Synthesis and Natural Products I, nstitute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
We report in this paper a novel Cu-catalyzed synthesis of polysubstituted 1-pyrrolines. The reaction of β,γ-unsaturated oxime esters 4 with terminal alkynes 5 in the presence of a catalytic amount of Cu(OAc) and 2,2'-biquinoline affords the corresponding 1,6-enynimines, which undergo a highly stereoselective Alder-ene reaction to afford 1-pyrrolines with concomitant generation of a quaternary carbon and a 2-azadiene motif. It represents an unusual [4+1] heteroannulation reaction wherein terminal alkynes act as a one carbon donor and are 1,1-difunctionalized.
View Article and Find Full Text PDFOrg Biomol Chem
November 2023
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan.
Polysubstituted furans were synthesized in one-pot through the EtZn-mediated coupling reaction between dibromoketones and monobromo carbonyl compounds and the subsequent β-elimination with bromoacetyl bromide. Polysubstituted pyrroles were also prepared in one-pot by addition of primary amines after the coupling reaction.
View Article and Find Full Text PDFChemistry
December 2023
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
Gold catalysis is an important method for alkyne functionalization. Here we report the gold-catalyzed formal [3+2] aminative cyclization of yndiamides and isoxazoles in a direct synthesis of polysubstituted diaminopyrroles, which are important motifs in drug discovery. Key to this process is the formation, and subsequent cyclization, of an α-imino gold Fischer carbene, which represents a new type of gold carbene intermediate.
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