Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 22, Pages 6187-6193Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01273a
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Funding
- NSFC [22208184, 21978144, 21776148]
- Support Plan on Science and Technology for Youth Innovation of Universities in Shandong Province [2019KJM002]
- Talents of High Level Scientific Research Foundation [6651118009, 6631115015, 6631110309]
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The controllable synthesis of spirooxindole-fused dibenzo[b,f]oxocines and chromans from oxindole-embedded four-atom synthons and dibrominated compounds has been achieved through [4 + 4] and [4 + 2] cyclization reactions respectively. Additionally, the indole-fused nine-membered oxa-heterocycles can be selectively accessed by the ring expansion of spirooxindole-fused dibenzo[b,f]oxocines through carbocation rearrangement.
The controllable synthesis of spirooxindole-fused dibenzo[b,f]oxocines and chromans from oxindole-embedded four-atom synthons and dibrominated compounds through, respectively, [4 + 4] and [4 + 2] cyclization reactions has been developed. In addition, the indole-fused nine-membered oxa-heterocycles also could be accessed switchably through the carbocation-rearrangement-initiated ring expansion of spirooxindole-fused dibenzo[b,f]oxocines by facile operation.
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