1859-90-1Relevant articles and documents
-
Jackson,Smith
, p. 989,997 (1965)
-
PdBr2-catalyzed direct synthesis of 2,3-disubstituted indoles via a tandem reaction between arylamines and α-diketones
Cabrera,Sharma,Ayala,Rubio-Perez,Amézquita-Valencia, Manuel
supporting information; experimental part, p. 6758 - 6762 (2012/01/04)
A direct PdBr2(BINAP)-complex catalyzed method has been developed to produce 2,3-disubstituted indoles by the reaction of arylamines with α-diketones under reductive (H2) conditions. The synthetic methodology involves a tandem reaction of three steps and all the organic intermediates were isolated and characterized, the reduction products in this sequence are chiral and present interesting enantiomeric excess. This report constitutes a new and different route to synthesize indoles and a plausible mechanism is also suggested.
Zeolites as Catalysts in the Fischer Indole Synthesis. Enhanced Regioselectivity for Unsymmetrical Ketone Substrates
Prochazka, Michal P.,Eklund, Lars,Carlson, Rolf
, p. 610 - 613 (2007/10/02)
The use of zeolites as catalysts in the Fischer indole synthesis has been studied on five unsymmetrical ketone substrates with 14 different zeolites.Both the corresponding phenylhydrazone and the parent ketone in the presence of phenylhydrazine were used as substrates.Zeolites which catalysed the indolization of the phenylhydrazones were also active in the direct conversion of the parent ketone.For substrates which gave mixtures of isomeric indoles under homogeneous, classical indolization conditions in acetic acid, it was found that the distribution of regioisomersof the indoles formed was altered considerably by zeolite catalysis and that the distribution was dependent on the type of zeolite used.A one-pot synthetic procedure for indole synthesis from the parent ketone and phenylhydrazine is described.