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Synthesis of indole derivatives from N ‐alkenyl‐ o ‐chloroanilines with zero‐valent nickel complex
Author(s) -
Rodriguez J. G.,
Canoira L.
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.5570220356
Subject(s) - chemistry , indoline , indole test , triphenylphosphine , toluene , medicinal chemistry , nickel , reaction mechanism , double bond , organic chemistry , stereochemistry , catalysis
Reaction of N ‐alkenyl‐ o ‐chloroanilines in toluene with tetrakis(triphenylphosphine)nickel (0) was carried out mainly to give indole and indoline derivatives in good yields. A detailed analysis of the reaction products has been done and it allows us to confirm the postulated mechanism of the cyclization reaction. Torsional hindrance around the NCCsp 2 bond seems to prevent the cyclization reaction.