Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 40, Pages 7393-7399Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob02099j
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Funding
- Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation
- CAMS Innovation Fund for Medical Sciences (CIFMS) [2016-I2M-3-009]
- Non-profit Central Research Institute Fund of Chinese Academy of Medical Sciences [2018PT35002]
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A mild and transition-metal-free approach for the synthesis of (E)-3-aryl-2,3,4,5-tetrahydro-1H-3-benzazonines via [2,3] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines with arynes is described. This protocol provides straightforward access to (E)-3-aryl-2,3,4,5-tetrahydro-1H-3-benzazonines in moderate to good yields with excellent diastereoselectivity. A broad range of functional groups, involving nitrile, esters, ketone and aryl halide, were well tolerated in this reaction.
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