Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 24, Pages 13751-13755Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02769
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Funding
- Robert A. Welch Foundation [F-0038]
- NIH-NIGMS [RO1-GM069445]
- UT Austin Center for Green Chemistry and Catalysis
- Alexander von Humboldt foundation
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Benzocyclobutenones 1a-1g undergo cycloreversion at 150 degrees C in m-xylene solvent to form transient alpha-oxo-ortho-quinodimethanes or ortho-quinoid ketene methides, which engage in intermolecular [4+2] cycloadditions With isatins 2a-2f to form 2-oxiiidole spirolactones 3a-3I. This process tolerates an array of different functional groups and substitution patterns, and is applicable to unprotected isatins 2b-2f bearing free NH-functionalities. The superior performance of isatins compared to other carbonyl based dienophiles was demonstrated and rationalized with the aid of quantum chemical calculations.
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