Search results for "Fischer indole synthesis"
showing 3 items of 3 documents
Functionalized 2-azabicyclo[3.3.1]nonanes. IV. synthesis of the indolo[3,2-f]morphan system.
1982
Abstract A short route to the 2-azabicyclo[3.3.1]nonan-7-one system is described. Condensation of 4-piperidones with diethyl 2-oxopropylphosphonate, followed by catalytic hydrogenation furnished the corresponding piperidylpropanones 6 which were cyclized with mercuric acetate in acetic acid to the target target bicyclic ketones 1 . The Fischer indole synthesis from 1 a afforded regioselectively the indole [3,2-f]morphan 2 , a new heteromorphan type.
Two-Step Route to Indoles and Analogues from Haloarenes: A Variation on the Fischer Indole Synthesis
2012
In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines.
The fischer indole synthesis of 8-methyl-5-substituted-1-oxo-β-carbolines: A remarkable high yield of a [1,2]-methyl migration.
1991
Abstract A very unusual high yield of rearranged products (via methyl migration) has been obtained in the Fischer indole cyclization of the 3-(2,5-dimethyl phenylhydrazone) of 2,3-piperidine dione (6b). When a less activated aromatic ring is present in the phenylhydrazone 6, such a behaviour is not observed and cyclization occurs essentially without rearrangement.