Synthesis of 2-alkyl-substituted benzimidazoles by thermal decomposition of 2-azidobenzenamines in the presence of an aldehyde

2-Substituted benzimidazoles were prepared by reaction of 2-azidoaminobenzenes with aldehydes under thermal conditions. The reaction probably proceeds via a sequential imine formation, azide decomposition forming a nitrene, and electrocyclization.

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Bibliographic Details
Published inSynthetic communications Vol. 36; no. 22; pp. 3425 - 3439
Main Authors Wallace, Jeffery M., Soederberg, Bjoern C. G., Hubbard, Jeremiah W.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 01.11.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUTED BENZIMIDAZOLES
nitrene
INTRAMOLECULAR CYCLIZATION
PALLADIUM-CATALYZED SYNTHESIS
alkaloids
benzimidazole
IONS
2-ARYLBENZIMIDAZOLES
ANILS
POLYPHOSPHORIC ACID
azide
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Summary:2-Substituted benzimidazoles were prepared by reaction of 2-azidoaminobenzenes with aldehydes under thermal conditions. The reaction probably proceeds via a sequential imine formation, azide decomposition forming a nitrene, and electrocyclization.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910600941497