Greener synthesis using hydrogen peroxide in ethyl acetate of alicyclic ring-fused benzimidazoles and anti-tumour benzimidazolequinones. Issue 36 (6th September 2017)

• Record Type: Journal Article
• Authors: Sweeney, Martin; Gurry, Michael; Keane, Lee-Ann J.; Aldabbagh, Fawaz
• Is Part Of: Tetrahedron letters. Volume 58:Issue 36(2017)
• Page Start: 3565
• Page End: 3567
• Publication Date: 2017-09-06
• Subjects: Annulations -- Green chemistry -- Heterocycles -- Quinones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.07.102
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: H2 O2 in EtOAc is a new cost-effective and green approach for synthesis. Sixteen oxidative cyclizations to give ring-fused [1, 2- a ]benzimidazoles. The easiest approach to ring-fused benzimidazolequinone anti-tumour agents available. Abstract: Environmentally-friendly and cost effective hydrogen peroxide in ethyl acetate was used to prepare in high yields pyrrolo[1, 2- a ]benzimidazoles from commercial o -(pyrrolidin-1-yl)anilines without the requirement for organic-aqueous extraction and chromatography. Six, seven and eight membered ring-fused analogues were similarly obtained in high yields with methanesulfonic acid required for the pyrido[1, 2- a ]benzimidazole. Anti-tumour benzimidazolequinone derivatives were obtained in high yield via the cyclization of 3, 6-dimethoxy-2-(cycloamino)anilines.