Carbon atom insertion into N-heterocyclic carbenes to yield 3,4-dihydroquinoxalin-2(1H)-ones

文献情報

出版日 2023-11-10

DOI 10.1039/D3QO01579C

インパクトファクター 5.281

著者

Justin S. Lamb, Futa Koyama, Noriyuki Suzuki, Yumiko Suzuki

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要旨

Carbon atom insertion into a cyclic framework is an attractive form of molecular editing since it can modify the core skeleton of a molecule, allowing for controlled increases in molecular size and complexity. We have discovered that when benzimidazoliums and 2-(methylsulfonyl)chromones were mixed under basic conditions, followed by the addition of a basic aqueous solution/mixture, the carbon atom located at position 2 of the chromone could be inserted into the in situ-generated N-heterocyclic carbenes (NHCs) to afford (Z)-3-(2-phenyl-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones, a scaffold found in numbers of bioactive compounds. Under the same conditions, 1-methyl-3-phenylbenzimidazolium iodide provided an unexpected pentacyclic product with a [1]benzopyrano[2,3-b]phenazine framework in an excellent yield presumably via a pathway involving a single-carbon transfer from the NHC.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry