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Thermal reactions of N ‐alkyl‐2‐benzylaniline and N ‐alkyl‐ N ′‐phenyl‐ o ‐phenylenediamine: An unusual route to 2‐phenylindole and 2‐phenylbenzimidazole
Author(s) -
Creencia Evelyn Cuevas,
Taguchi Kei,
Horaguchi Takaaki
Publication year - 2008
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.5570450331
Subject(s) - chemistry , alkyl , phenazine , acridine , medicinal chemistry , ring (chemistry) , anthracene , stereochemistry , organic chemistry
Thermal cyclization reactions of N ‐alkyl‐2‐benzylaniline 1a‐d and N ‐alkyl‐ N ′‐phenyl‐ o ‐phenylenediamine 2a‐b were carried out expecting to get seven‐membered heterocyclic compounds. However, the results show that aside from the formation of the normally expected six‐membered ring products of acridine 5 , anthracene 6 , and phenazine 8 , thermal cyclization of N ‐alkyl‐2‐benzylaniline and N ‐alkyl‐ N ′‐phenyl‐ o ‐phenylenediamine also resulted to the unexpected formation of 2‐phenylindole 3 and 2,3‐diphenylindole 4 , and 2‐phenylbenzimidazole 7 , respectively.