Synthesis of chromeno[4,3-b]quinolines and spirobenzofuran-3,3′-quinolines through silver-mediated Appel reaction/C–Br bond cleavage/double selective rearrangement sequence

文献情報

出版日 2019-05-06

DOI 10.1039/C9QO00417C

インパクトファクター 5.281

著者

Hong-Ping Zhao, Xiao-Pan Ma, Shu-Min Nie, Yuhong Xiao, Dong-Liang Mo

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要旨

Various chromeno[4,3-b]quinolines and spirobenzofuran-3,3′-quinolines were prepared in good to excellent yields through a reduction and silver-mediated Appel reaction/sequential C–Br bond cleavage/double selective rearrangement cascade strategy from easily available chromeno[4,3-b]indolecarbaldehydes. Cross-over experiments revealed that the group migration occurred intramolecularly and the electronic effect on styrenyl groups had a little effect on the migration step. Two novel quinoline scaffolds were easily prepared on a gram scale by simple operation.

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

Synthesis of chromeno[4,3-b]quinolines and spirobenzofuran-3,3′-quinolines through silver-mediated Appel reaction/C–Br bond cleavage/double selective rearrangement sequence

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