370069-26-4Relevant articles and documents
Two-step solution-phase synthesis of novel benzimidazoles utilizing a UDC (Ugi/de-Boc/cyclize) strategy
Tempest, Paul,Ma, Vu,Thomas, Samuel,Hua, Zheng,Kelly, Michael G.,Hulme, Christopher
, p. 4959 - 4962 (2001)
The novel solution-phase synthesis of an array of biologically relevant benzimidazoles in a simple two-step procedure is revealed. Transformations are carried out in excellent yield by condensation of mono-Boc protected ortho-phenylene diamine and supporting Ugi reagents. Subsequent acid treatment and evaporation affords benzimidazoles in good to excellent yield. The described protocol represents a highly attractive solution-phase procedure for the rapid generation of benzimidazole libraries.
MCC/SNAr methodology. Part 1: Novel access to a range of heterocyclic cores
Tempest, Paul,Ma, Vu,Kelly, Michael G.,Jones, Wyeth,Hulme, Christopher
, p. 4963 - 4968 (2001)
The novel solution-phase syntheses of arrays of biologically relevant indazolinones, benzazepines and benzoxazepines, utilizing multi-component condensation (MCC)/SNAr methodology is reported. Reaction of commercially available 2-fluoro-5-nitrobenzoic acid with an aldehyde, isonitrile and a primary amine tethered to a Boc-protected internal amino or hydroxyl nucleophile, affords the Ugi product in good yield. Subsequent acid treatment followed by proton scavenging promotes cyclization of internal amino nucleophiles to a variety of ring sizes. Base treatment alone is sufficient to generate benzoxazepines. Interestingly, this communication also introduces a highly efficient two-step route to benzimidazoles.