Synthetic access to poly-substituted 6-alkoxyindoles from 1,3-cyclohexanediones and nitroolefins through facile aromatization reaction.

Abstract

6-Alkoxy-3-arylindoles were efficiently prepared from 1,3-cyclohexanedione enol ethers and beta-nitrostyrenes. Michael addition using the kinetically generated enolate, followed by Zn reduction of a nitro group of the resulting adducts produced the nitrones which were then treated with acetic anhydride to induce aromatization by dehydration and N-acetylation, which furnished the desired indoles by the DDQ oxidation. This methodology provides an easy entry toward various poly-substituted 6-alkoxyindoles.

• Authors: Li-Jian Ma, Xiao-Xia Li, Tomoyo Kusuyama, Ibrahim El-Tantawy El-Sayed, Tsutomu Inokuchi
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 74 Issue 23 Pg. 9218-21 (Dec 04 2009) ISSN: 1520-6904 [Electronic] United States
• PMID: 19894747 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkenes
• Cyclohexanones
• Ethers
• Hydrocarbons, Aromatic
• Indoles
• Nitro Compounds
• Styrenes
• 1,3-cyclohexanedione

Topics

• Alkenes (chemistry)
• Cyclohexanones (chemistry)
• Ethers (chemistry)
• Hydrocarbons, Aromatic (chemistry)
• Indoles (chemical synthesis)
• Methods
• Nitro Compounds (chemistry)
• Styrenes (chemistry)