Electrophilic substitution reaction of indole,part XXIV: Synthesis,characterization, and crystal structure of a novel heterocyclic compound |
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| Authors: | Anupam Nayak Utpal Dutta Thierry Prangé Julie Banerji |
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| Affiliation: | 1. Centre of Advanced Studies on Natural Products including Organic Synthesis, Department of Chemistry, University College of Science and Technology, University of Calcutta, Kolkata‐700 009, India;2. Laboratoire de cristallographie et RMN Biologiques (UMR 8015 CNRS), Université Paris Descartes. 4, Av de l'Observatoire, 75006 Paris, France |
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| 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 (1H and 13C) 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). |
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