Thermal reactions of N-alkyl-2-benzyl aniline and N-alkyl-N'-phenyl-o-phenylenediamine: An unusual route to 2-phenylindole and 2-phenylbenzimidazole

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 acr...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 45; no. 3; pp. 837 - 843
Main Authors Creencia, Evelyn Cuevas, Taguchi, Kei, Horaguchi, Takaaki
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.05.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MURRAYA-KOENIGII
REDUCTION
TERTIARY-AMINES
CONVENIENT
TERVALENT PHOSPHORUS REAGENTS
CARBAZOLE ALKALOIDS
NITROSO-COMPOUNDS
BENZIMIDAZOLES
DERIVATIVES
INDOLES
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Summary: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 fort-nation of 2-phenylindole 3 and 2,3-diphenylindole 4, and 2-phenylbenzimidazole 7, respectively.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570450331