Tetrahedron

Diborane as a reducing agent-VI the novel reduction of indole-1-carboxaldehydes to 1-methyl-indoles, di (indolyimethyl) ethers and indolylmethyl indolines

KM Biswas, R Dhara, S Roy, H Mallik

Index: Biswas, M. Kshetra; Dhara, Rabindranath; Roy, Sumita; Mallik, Haimanti Tetrahedron, 1984 , vol. 40, # 21 p. 4351 - 4357

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Citation Number: 6

Abstract

Reduction of the indole-1-carboxaldehydes (1a-1f) with borane/THF gives the 1- methylindoles (4) in 42-91-% yields together with the di (indolylmethyl) ethers (8), the indolyl- methyl indolines (7), the unsymmetric ether (10) and the indolenine (11) as the minor products, except 7a. 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 7a and 7b from 1a ...