Trimethyl Orthobenzoate as a1-C1-Phenyl-Synthon for Functionalization of 3-Unsubstituted Indoles
The methylindoles 2a and 2b are regioselectively functionalized with trimethyl orthobenzoate at C-3 by means of proton catalysis. The first stage is the formation of the key compounds, 3-indolyl-phenyl-methoxycarbenium ions 3. These can then be dealkylated under mild conditions using nucleophilic s...
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| Main Authors: | , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1985-05-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9660 |
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| Summary: | The methylindoles 2a and 2b are regioselectively functionalized with trimethyl orthobenzoate at C-3 by means of proton catalysis. The first stage is the formation of the key compounds, 3-indolyl-phenyl-methoxycarbenium ions 3. These can then be dealkylated under mild conditions using nucleophilic solvent to form the 3-benzoylindoles 5a and 5b. The highly stabilized cations 3, whether generated in situ or directly applied as a salt also represent potent precursors in the derivation of the 3,3'-bisindolyl-phenyl-methane dyes 4.
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| ISSN: | 0009-4293 2673-2424 |