Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 78, No. 8, 2009, pp.2033-2040
Published online, 13th April, 2009
DOI: 10.3987/COM-09-11706
Synthesis of Bis(indolyl)methane Derivatives by Acid-Catalyzed Reactions of Indoles with Vinyl Ethers

Kazuhiro Kobayashi,* Yuu Shirai, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

2,2-Bis(indol-3-yl)propane derivatives have been synthesized by the reaction of 3-nonsubstituted indoles with 2-methoxypropene in dichloromethane in the presence of a catalytic amount of (±)-camphor-10-sulfonic acid. The similar treatment of 3-substituted indoles with 2-methoxypropene under the same conditions has resulted in the formation of 2,2-bis(indol-2-yl)propanes. The reaction of 3-substituted indoles with ethoxyethene has afforded bis(indol-1- yl)ethanes. Subsequently, 3-substituted indoles have proved to react with excess vinyl ethers under the same conditions to afford the corresponding 1-(1-alkoxyalkyl)indoles.