Diborane as a reducing agent - VI the novel reduction of indole-1-carboxaldehydes to 1-methyl- indoles,di(indolyimethyl) ethers and indolylmethyl indolines |
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Authors: | Kshetra M Biswas Rabindranath Dhara Sumita Roy Haimanti Mallik |
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Institution: | Department of Chemistry, University College of Science, University of Calcutta, 92, Acharya Prafulla Chandra Road, Calcutta-700009, India |
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Abstract: | Reduction of the indole-1-carboxaldehydes (-) with borane /THF gives the 1-methylindoles () in 42-91-% yields together with the di(indolylmethyl)ethers (), the indolyl-methyl indolines (), the unsymmetric ether() and the indolenine () as the minor products, except . This appears to be the first report on the formation of symmetric ethers in the borane/THF reduction of an oxygen function. The formation of and from and implies that electrophilic substitution takes place primarily at position 3 of 3-substituted indoles, did not form the corresponding probably because of steric hindrance. These results are discussed in relation to the mechanisms of borane/THF reduction, origin of the different products and electrophilic substitution in 3-substituted indoles. |
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