Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 7, Issue 23, Pages 4862-4870Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b914580j
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Funding
- Natural Sciences and Engineering Research Council of Canada
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Readily accessible 3-alkoxycarbonyl-6-hydroxy-5-halocoumarins can be converted into 4-halo-5-hydroxyindoles by a sequence whose essential steps are conjugate reduction or conjugate addition, decarboxylation, lactone opening with ammonia, phenolic oxygen protection, Hofmann rearrangement to an N-Boc ethylamine, oxidation to a quinone and deprotection of the nitrogen. The resulting beta-aminoethyl quinone cyclizes to a mixture of quinone imine and indole, and the imine tautomerizes to the indole spontaneously or on treatment with rhodium on alumina.
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