Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 47, Pages 16977-16983Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603045
Keywords
amines; heterocycles; indenamine; isoindolinone; ynones
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Funding
- NSFC [21402106, 21475075, 21475074]
- SRF for ROCS, SEM [20141685]
- Shandong Natural Science Foundation [ZR2014BQ024, ZR2013BM007]
- Higher Educational Science and Technology Program [J15LA02]
- Qufu Normal University for Research Start-up Foundation [bsqd20130115]
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Herein we describe a reaction of ortho-carbonylated alkynyl-substituted arylaldehydes with common primary amines that can provide functionalized isoindolinone and 3-hydroxylindenamine products in high yields. Depending on the substituent size of primary amines, two distinct reaction pathways were exploited selectively, that are, an initial aza-conjugate addition followed by hydrogen transfer to access isoindolinone framework and a unique oxa-conjugate addition followed by Petasis-Ferrier rearrangement to afford indenamine derivatives. In the presence of Et3N, the reaction property of small primary amines was changed, proceeding to afford 3-hydroxylindenamine derivatives efficiently. These products contain interesting substructures that exist in many natural products and bioactive molecules. The reaction features contain the use of transition-metal-free catalysts, simple operation, broad substrate scope, and product diversity.
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