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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

✍ Scribed by Evelyn Cuevas Creencia; Kei Taguchi; Takaaki Horaguchi

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
454 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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.

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