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Paper | Regular issue | Vol 65, No. 1, 2005, pp.37-48
Published online, 2nd November, 2004
DOI: 10.3987/COM-04-10200
First Isolation of Both Indolylcarbinols and Diindolylalkanes from Microwave-assisted Acid (Clay)-catalysed Reaction of Indoles with Diethyl Ketomalonate

Manas Chakrabarty,* Sulakshana Karmakar, and Yoshihiro Harigaya

*Department of Chemistry, Bose Institute, 93/1, A. P. C. Road, Kolkata-700009, India

Abstract

Indoles (1a-f) react with diethyl ketomalonate on montmorillonite K10 clay under microwave irradiation to furnish expeditiously (1-4 min) the corresponding indol-3’-ylcarbinols (2a-f; 20-45%) and the respective diindolylalkanes (3a-f; 5-35%), which constitute the first direct evidence for the intermediacy of indolylcarbinols in the formation of diindolyl-alkanes from the acid-catalysed reaction of indoles with aldehydes and ketones.