Electrophilic substitution reaction of indole, part XXIV: Synthesis, characterization, and crystal structure of a novel heterocyclic compound

✍ Scribed by Anupam Nayak; Utpal Dutta; Thierry Prangé; Julie Banerji

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2011
• Tongue: English
• Weight: 215 KB
• Volume: 48
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.554

✦ Synopsis

Abstract

The reaction of indole with cyclohexanone in the presence of the Lewis acid, boron trifluoride diethyl etherate, resulted in the synthesis of a novel and interesting product (1) in addition to the bis(indolyl)methane system (2). The structure of this novel compound has been determined by NMR (^1^H and ^13^C) and X‐ray crystal structure analysis. Compound 1 is a (1:2) addition reaction product of indole with cyclohexanone. The spiro six‐membered ring is in the classic chair conformation. An epoxide bridge at C‐4a/C‐10b and the two hydroxyl groups at C‐5a, C‐10a are all on the same side of the central five membered ring. J. Heterocyclic Chem., (2011).