Nucleophilic substitution reaction on the nitrogen of indole nucleus: A novel synthesis of 1-aryltryptamines
1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nitrogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles,
Nucleophilic substitution reaction on the nitrogen of indole nucleus: Formation of 1-(indol-3-yl)indoles upon reaction of 1-hydroxyindoles with indole in formic acid
1-(Indol-3-yl)indoles are obtained in excellent to good yields by the reaction of 1-hydroxyindoles with indole in 85% formic acid. Their structures are determined by X-Ray crystallographic analysis and chemical correlations. The unprecidented SN2 mechanis
Synthesis of Indole and Oxindole Derivatives from N-β-Alkenyl-o-chloroanilines and N-β-Alkenyl-o-chloroanilides with Tetrakis(triphenylphosphine)nickel(0) and Zerovalent Pyridine-Nickel Complexes.
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Canoira, Laureano,Rodriguez, J. Gonzalo
p. 646 - 666
(2007/10/02)
Synthesis of Oxindole Derivatives from N-Alkenyl-o-Chloroanilides with Zero-Valent Nickel Complex
Oxindole derivatives have been obtained from N-alkenyl-o-chloroanilides by reaction with tetrakis(triphenylphoaphine)nickel(0) in toluene as solvent in good yields.A detailed analysis of all the products of the reaction allows to confirm the postulated mechanism of the cyclization reaction.The o-chloroanilides of the 3-cyclohexenylacetic acid fails in the cyclization reaction, since the torsional hindrance seems to avoid that the endocyclic double bond may be orthogonally to the ortho-?-nickel complex intermediate on the aromatic ring.
Canoira, L.,Rodriguez, J. G.
p. 1511 - 1518
(2007/10/02)
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