Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 66, Pages 16799-16805Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201702622
Keywords
alkylation; heterocycles; regioselectivity; spiro compounds; synthesis design
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Funding
- Japan Society for the Promotion of Science (JSPS) [JP15K07853]
- JSPS Core-to-Core Program
- Grants-in-Aid for Scientific Research [15K07853, 16K08158] Funding Source: KAKEN
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An efficient route to highly substituted indoles was developed. It included regioselective functionalization of tetrahydroindol-4(5H)-ones, prepared by ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with primary amines, and subsequent oxidation. The 6-substituted indoles were synthesized from a readily available 5substituted cyclohexane-1,3-dione-2-spirocyclopropane. The synthesis of 5-and 7-substituted indoles was achieved by regioselective electrophilic alkylation of tetrahydroindol-4(5H)-one, followed by oxidation. The 4-substituted indoles were synthesized by nucleophilic alkylation of the corresponding pyrrole derivative, which was prepared by partial oxidation of tetrahydroindol-4(5H)-one, and sequential oxidation. The synthesis of 4-substituted indoles was also accomplished by palladium-catalyzed coupling of 4-hydroxyindole-derived triflates. Furthermore, the synthesis of 4,5,6,7-tetrasubstituted indoles was achieved by using these regioselective alkylations.
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