title: The Thermal Instability of 2,4 and 2,6-N-Alkylamino Disubstituted and 2-N-Alkylamino Substituted Nitrobenzenes in Weakly Alkaline Solution:sec-Amino Effect.
abstract: We report herein the preparation of two families of secondary amines by the reactions of two equivalents of monoamines with either 2,4 or 2,6-difluoronitrobenzenes inN,N-dimethylacetamide in the presence of anhydrous potassium carbonate, as precursors of biologically important nitric oxide donatingN-nitrosamines. In both instances, these compounds could be prepared in quantitative yield when the reaction temperature was held below 130°C. Above this reaction temperature, an unexpected cyclization reaction between the nitro and newly formed adjacent secondary amine group leads to the formation of benzimidazole or quinoxaline rings in low yields. Reasonable reaction mechanisms for the cyclization reaction are proposed.
authors.affiliation: Department of Chemistry, Central Michigan University, Mt. Pleasant, MI-48858, USA.
authors.forename: Christopher
authors.initials: C
authors.lastname: Walczak
authors.affiliation: Department of Chemistry, Central Michigan University, Mt. Pleasant, MI-48858, USA.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Payne
authors.affiliation: Department of Chemistry, Central Michigan University, Mt. Pleasant, MI-48858, USA.
authors.forename: Colin B
authors.initials: CB
authors.lastname: Wade
authors.affiliation: Department of Chemistry, Central Michigan University, Mt. Pleasant, MI-48858, USA.
authors.forename: Matthew
authors.initials: M
authors.lastname: Yonkey
authors.affiliation: Department of Chemistry, Central Michigan University, Mt. Pleasant, MI-48858, USA.
authors.forename: Melissa
authors.initials: M
authors.lastname: Scheid
authors.affiliation: Department of Chemistry, Central Michigan University, Mt. Pleasant, MI-48858, USA.
authors.forename: Alec
authors.initials: A
authors.lastname: Badour
authors.affiliation: Department of Chemistry, Central Michigan University, Mt. Pleasant, MI-48858, USA.
authors.forename: Dillip K
authors.initials: DK
authors.lastname: Mohanty