Herein, we report an efficient 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed tandem intermolecular amidation and regioselective intramolecular 6--dig cyclization of alkynyl esters to efficiently access pyrazine-1(2)-one scaffolds. This organo-catalyzed [5 + 1] annulation features a broad substrate scope concerning both annulating partners. Total syntheses of peramine and formal syntheses of dibromophakellin natural products were achieved to show the application potential of the method.
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http://dx.doi.org/10.1021/acs.joc.3c02157 | DOI Listing |
Inorg Chem
January 2025
Inner Mongolia Engineering Research Centre of Lithium-Sulfur Battery Energy Storage, Inner Mongolia Key Laboratory of Solid State Chemistry for Battery, College of Chemistry and Materials Science, Inner Mongolia Minzu University, Tongliao 028000, People's Republic of China.
In the era of global warming, the conversion of carbon dioxide into high-value products has become a widely scrutinized emerging mitigation strategy. Metalation of bpy-containing MOF-253 led to the synthesis of MOF-253-0.5Ag, which acts as an efficient catalyst for the carbonylative cyclization of CO with alkyne molecules (such as propynyl alcohols and propynyl amines) at room temperature and ambient CO pressure, yielding the corresponding α-alkyl cyclic carbonates and oxazolidinones, thus endowing the catalytic system with bifunctional characteristics.
View Article and Find Full Text PDFAsian J Org Chem
January 2025
Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, New Jersey 08854, USA.
A one-pot process was developed to synthesize in moderate to high yield a series of 2-substituted indoles and 7-azaindoles starting from 2-iodo--mesylarylamines and terminal alkynes in the presence of CuO in DMF at 90-120 °C. Without isolation of any intermediate, our optimized conditions enabled the introduction of ester, phenyl, hydroxymethyl, hydroxyethyl, -Boc-aminomethyl, and methyl at the 2-postion of indoles and 7-azaindoles. The reaction tolerates a variety of substrates containing halogens, or acid- or base-sensitive functional groups without requiring a Pd catalyst, a ligand, or a base.
View Article and Find Full Text PDFMolecules
November 2024
Hunan Province Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China.
Thieno[3,2-]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-]thiophene and selenopheno[3,2-]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I/NaSO or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials.
View Article and Find Full Text PDFEuropean J Org Chem
November 2024
Department of Chemistry, University of Rochester, Rochester, NY 14627.
This manuscript describes a study of diverse reaction outcomes that stem from the ionization of -alkynyl-Prins adducts. Experimental results have demonstrated unexpected behavior in the nitrogen-containing systems compared to the analogous oxygen derivatives derived from -Prins/-Nazarov sequences. In-depth experimental studies and computational analysis revealed an intricate mechanism involving competing -Nazarov and -Nazarov pathways.
View Article and Find Full Text PDFChem Commun (Camb)
December 2024
Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
A base-promoted cascade 5- cyclization/carboxylation of -alkynylsulfamides with CO has been accomplished, furnishing a variety of benzosultam-containing acrylates in good yields by using CO as the carboxylic source. Notably, in the case of substrates bearing a TMS-alkyne motif, the -dicarboxylation products were generated unprecedentedly.
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