Microwave assisted one-pot transformation has been developed for the synthesis of biologically significant polysubstituted furoquinoxalines in good to excellent yields through a copper(II) catalyzed three-component coupling of o-phenylenediamine, ethylglyoxalate, and terminal alkyne, known as A(3)-coupling, followed by 5-endo-dig cyclization.
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http://dx.doi.org/10.1021/ol502072k | DOI Listing |
Org Lett
December 2024
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline -oxides with -alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2'-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.
View Article and Find Full Text PDFNanoscale Adv
October 2024
Department of Medical Engineering, Al-Nisour University College Baghdad Iraq.
In this study, we have prepared a novel bis-Schiff-base copper(ii) complex by modifying FeO with acetylacetone functionalities and subsequently forming a Schiff base with 2-picolylamine and CuCl through a template method. Immobilization of 2,4-pentanedione and its reaction with 2-picolylamine enabled the synthesis of 1,3-diketimines (HNacNac) as an anionic ligand. This unique design resulted in a tetradentate N coordination sphere for copper(ii) ion complexation.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
Department of Chemistry, Georgetown University, Box 571227, 20057-1227, Washington, DC, USA.
α-substituted ketones are important chemical targets as synthetic intermediates as well as functionalities in natural products and pharmaceuticals. We report the α-acetylation of C(sp)-H substrates R-H with arylmethyl ketones ArC(O)Me to provide α-alkylated ketones ArC(O)CHR at RT with BuOOBu as oxidant via copper(I) -diketiminato catalysts. Proceeding via alkyl radicals R•, this method enables α-substitution with bulky substituents without competing elimination that occurs in more traditional alkylation reactions between enolates and alkyl electrophiles.
View Article and Find Full Text PDFChem Sci
September 2024
Department of Chemistry, Michigan State University East Lansing Michigan 48824 USA
The prenyl group is present in numerous biologically active small molecule drugs and natural products. We introduce benzylic C-H alkenylation of substrates Ar-CH with alkenylboronic esters (CH)OB-CH[double bond, length as m-dash]CMe as a pathway to form prenyl functionalized arenes Ar-CHCH[double bond, length as m-dash]CMe. Mechanistic studies of this radical relay catalytic protocol reveal diverse reactivity pathways exhibited by the copper(ii) alkenyl intermediate [Cu]-CH[double bond, length as m-dash]CMe that involve radical capture, bimolecular C-C bond formation, and hydrogen atom transfer (HAT).
View Article and Find Full Text PDFJ Mater Chem B
November 2024
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. China.
Cancer, a pressing global health challenge, is characterized by its rapid onset and high mortality rates. Conventional treatment methods prove insufficient in achieving the desired therapeutic outcomes, underscoring the critical need to identify an effective and safe approach for cancer treatment. In this study, a copper-doped nanoparticle known as Cu-DOX@ZIF-90 is designed by incorporating copper(II) (Cu(II)) and encapsulating doxorubicin (DOX) within ZIF-90.
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