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: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 81, No. 5, 2010, pp.1169-1182
Published online, 26th February, 2010
DOI: 10.3987/COM-10-11904
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Oscar R. Suárez-Castillo,* Myriam Meléndez-Rodríguez, Indira C. Cano-Escudero, Sandra Luz De Ita-Gutiérrez, Maricruz Sánchez-Zavala, Martha S. Morales-Ríos, and Pedro Joseph-Nathan

*Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184, Mexico

Abstract

The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and α-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl4 gave α-bromoindole 6 which after treatment with ROH/3Å molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products, together with minor amounts of α-alkoxyindoles 9a-d. The reversed regioselectivity was achieved in the absence of molecular Sieves to give α-alkoxyindoles 9a-d as the main products, while no traces of Z- or E-8a-d were detected.