4.6 Article

Investigation on the Synthesis, Application and Structural Features of Heteroaryl 1,2-Diketones

期刊

ACS OMEGA
卷 7, 期 30, 页码 26650-26660

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acsomega.2c02914

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资金

  1. National Science Foundation [CHE-1760393]
  2. NKU Center for the Integration of Science and Mathematics, NKU UR-STEM Program
  3. Department of Chemistry and Biochemistry
  4. Robert A. Welch Foundation at the Department of Chemistry at the University of Texas Rio Grande Valley [BX-0048]

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A methodology for the synthesis of unsymmetrical heteroaryl 1,2-diketones using enones, a palladium catalyst, and an oxidant is reported. The lowest energy conformations of the synthesized compounds were analyzed using density functional theory.
A set of unsymmetrical heteroaryl 1,2-diketones were synthesized by a heteroarylation/oxidation sequence with up to 65% isolated yields. Palladium catalyst XPhos Pd G4 and SeO2 were the key reagents used in this methodology, and microwave irradiation was utilized to facilitate an efficient and ecofriendly process. The application of heteroaryl 1,2-diketones is demonstrated through the synthesis of an unsymmetrical 2-phenyl-3-(pyridin-3-yl)quinoxaline (5a) from 1-phenyl-2-(pyridin-3-yl)ethane-1,2-dione (4a). The lowest energy conformations of 4a and 5a were located using Density Functional Theory (DFT) at the M06-2X/def2-TZVP level of theory. Two lowest energy conformations of 4a differ with respect to the position of the N atom in the pyridyl ring and 0.27 kcal/mol energy difference between them corresponds to 60.4 and 39.6% at 50 ? in toluene. Four lowest energy conformations for 5a have the energy differences of 0.01, 0.03 and 0.07 kcal/mol that corresponds to 26.0, 25.7, 24.9 and 23.4%, respectively. A comparison of 4a and 5a to the less hindered analogs (oxalyl chloride and oxalic acid) is used to investigate the structural features and bonding using Natural Bond Orbital (NBO) analysis.

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