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Synthesis of oxindole derivatives from N ‐alkenyl‐ o ‐chloroanilides with zero‐valent nickel complex
Author(s) -
Canoira L.,
Rodriguez J. G.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220609
Subject(s) - chemistry , oxindole , nickel , toluene , triphenylphosphine , ring (chemistry) , medicinal chemistry , double bond , solvent , reaction mechanism , organic chemistry , catalysis
Oxindole derivatives have been obtained from N ‐alkenyl‐ o ‐chloroanilides by reaction with tetrakis(triphenylphosphine)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 ‐σ‐nickel complex intermediate on the aromatic ring.