96631-67-3Relevant academic research and scientific papers
Development of madelung-type indole synthesis using copper-catalyzed amidation/condensation strategy
Abe, Masahiro,Denneval, Charline,Nozawa-Kumada, Kanako,Kondo, Yoshinori
, p. 900 - 909 (2016/07/06)
A new method for Madelung-type indole synthesis was investigated, and it was found that the amidation of 2-iodophenylacetonitrile with various alkanamides proceeds smoothly in the presence of CuI and a diamine ligand. The subsequent cyclization of the C-N
SYNTHESIS OF DIHYDRO-1H-PYRROLO- AND TETRAHYDROPYRIDOINDOLES VIA A MODIFIED MADELUNG REACTION
Verboom, W,Orlemans, E.O.M.,Berga, H.J.,Scheltinga, M.W.,Reinhoudt, D.N.
, p. 5053 - 5064 (2007/10/02)
1-(2-Methylphenyl)lactams 9, having different electron -withdrawing groups at the benzylicposition, cyclize under the influence of sodium hydride or potassium tert-butoxyde.Depending on the ring size of the lactam moiety dihydropyrrolo- (10), tetrahydropyridoindole (11), or dihydro-1H-1-benzazepine (12) derivatives are formed.Pyrroloindole 10c has been converted into the corresponding quione 15b.Starting from naphthaleneacetonitrile 20, prepared in 5 steps from 2,3-dichloronaphthoquinone, the 5,10-dioxo-1H-pyrollobenzindole 22 is obtained upon treatment with base and subsequent oxidation of the protected hydroquinone function with ceric ammonium nitrate.
THE MADELUNG SYNTHESIS OF DIHYDRO-1H-PYRROLO- AND TETRAHYDROPYRIDO-INDOLES UNDER MILD CONDITIONS
Verboom, W.,Berga, W. P.,Trompenaars, W. P.,Reinhoudt, D. N.
, p. 685 - 688 (2007/10/02)
Benzeneacetonitriles substituted with lactam moieties in the ortho-position cyclize under the influence of a base, dependent on the ring-size of the lactam function, to dihydropyrrolo-,tetrahydropyridoindole or dihydro-1-benzazepin derivatives, respectively.
