A copper-catalyzed domino addition/cyclization reaction was developed to synthesize novel benzoselenazole-linked 1,2,3-triazole and tetracyclic fused 12-benzo[4,5]selenazole[2,3-]quinazolin-12-one derivatives from isoselenocyanates. This domino reaction efficiently constructed multiple new chemical bonds in a single step, forming either four (one C-Se and three C-) or three (one C-Se and two C-) bonds. The reaction offers several key advantages, including mild conditions, broad substrate compatibility, and straightforward and safe operation. It presents a new method for synthesizing , Se-containing polycyclic compounds, which have potential interest in medicinal chemistry. Notably, some of the synthesized compounds exhibited anticancer activity with IC values below 20 μmol L against T24 human bladder cancer cells.
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http://dx.doi.org/10.1021/acs.joc.4c02660 | DOI Listing |
J Org Chem
January 2025
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China.
A copper-catalyzed domino addition/cyclization reaction was developed to synthesize novel benzoselenazole-linked 1,2,3-triazole and tetracyclic fused 12-benzo[4,5]selenazole[2,3-]quinazolin-12-one derivatives from isoselenocyanates. This domino reaction efficiently constructed multiple new chemical bonds in a single step, forming either four (one C-Se and three C-) or three (one C-Se and two C-) bonds. The reaction offers several key advantages, including mild conditions, broad substrate compatibility, and straightforward and safe operation.
View Article and Find Full Text PDFJ Org Chem
January 2025
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, P. R. China.
An effective and economical copper-catalyzed approach for the synthesis of phosphorylated 1-isochromenes is reported. This method is the first example of focus on ketone phosphonylation to establish a C-P bond and 6-- cyclization to construct a C-O bond between aryl- and alkyl-substituted alkynylketones and H-phosphinate esters, H-phosphites, and H-phosphine oxides, resulting in chemo- and regioselective phosphorylated 1-isochromenes with moderate to excellent yields under smooth reaction conditions.
View Article and Find Full Text PDFJ Org Chem
September 2024
Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Hunan Province Key Laboratory of Green Organic Synthesis and Application, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
A convenient protocol for synthesis of unsymmetrical 2-methylpyridines from acetyl ketones, ammonium salts and tertiary amines is described. The construction of two C-C bonds and two C-N bonds via [2 + 2 + 1 + 1] four-component domino cyclization reaction is achieved using Cu(OTf) as catalyst in one pot. This cyclization reaction shows good selectivity and produces multisubstituted 2-methylpyridine derivatives in good yields with various functional groups.
View Article and Find Full Text PDFJ Org Chem
September 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER), Mohali, Sector 81, S.A.S. Nagar, Manauli (PO), Mohali 140306, Punjab, India.
Herein, we report a copper-catalyzed protocol to access unsymmetrical triarylmethanes containing both indolizine and the chromone scaffolds in the same molecule via a 5--dig cyclization of 2-(2-enynyl)-pyridines followed by reaction with 2-hydroxyaryl enaminones. A variety of 2-hydroxyaryl enaminones and 2-(2-enynyl)-pyridines were subjected to reaction under the optimal reaction conditions, and the respective triarylmethanes were obtained in good to excellent yields.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6, Canada.
A reagent-controlled diastereodivergent copper-catalyzed borylative difunctionalization is reported. The formation of Lewis adducts that guide selectivity is commonly invoked in organic reaction mechanisms. Using density functional theory calculations, we identified BpinBdan as a sterically similar and less Lewis acidic alternative to Bpin.
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