![2-Bromodibenzo[b,d]furan structure](https://static.chemtradehub.com/structs/86-/86-76-0-1814.webp "2-Bromodibenzo[b,d]furan structure")
Redox-triggered dearomative [5 + 1] annulation of indoles with O-alkyl ortho-oxybenzaldehydes for the synthesis of spirochromanes
Literature Information
Publication Date
2022-02-11
DOI
10.1039/D1QO01755A
Impact Factor
5.281
Authors
Hongmei Sun, Xiaomei Zhang
View Original
Abstract
The dearomative [5 + 1] annulation of 2-methylindoles with new five-membered synthons O-alkyl ortho-oxybenzaldehydes was developed unprecedentedly through cascade [1,5]-hydride transfer/dearomative cyclization in HFIP for the synthesis of spirochromanes bearing the 2-methylindolenine skeleton. In addition, the dual alkylation of the methyl group of 2-methylindolenines was achieved by sequential operation through the redox neutral [5 + 1] annulation with the second five-membered synthon N-alkyl ortho-aminobenzaldehyde, providing the chromane and tetrahydroquinoline fused spiroindolenines in good yields. Furthermore, the auxiliary group that facilitates the hydride transfer process could be simply removed.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
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1-(Hexopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl 3-phenylacrylate
CAS Number:
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