A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics

Behrouz, Somayeh; Kühl, Nikos; Klein, Christian

doi:10.1016/j.tetlet.2021.153342

Cited by 2 publications

(1 citation statement)

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“…Amidine derivatives are commonly used for the synthesis of many important heterocycles such as imidazoles, triazoles, thiazoles, oxadiazoles, pyrimidines, pyridines and triazines. The amidine moiety is a key pharmacophore in many biologically active compounds [57][58][59][60][61][62][63]. 1,8-Diazabicyclo [5.4.0]undec-7-ene (DBU) and some other amidines are used as organocatalysts in organic synthesis [64][65][66][67][68].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide)

et al. 2021

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A series of novel cobalt bis(dicarbollide) based amidines were synthesized by the nucleophilic addition of primary and secondary amines to highly activated B-N+≡C–R triple bond of the propionitrilium derivative [8-EtC≡N-3,3′-Co(1,2-C2B9H10)(1′,2′-C2B9H11)]. The reactions with primary amines result in the formation of mixtures of E and Z isomers of amidines, whereas the reactions with secondary amines lead selectively to the E-isomers. The crystal molecular structures of E-[8-EtC(NMe2)=HN-3,3′-Co(1,2-C2B9H10)(1′,2′-C2B9H11)], E-[8-EtC(NEt2)=HN-3,3′-Co(1,2- C2B9H10)(1′,2′-C2B9H11)] and E-[8-EtC(NC5H10)=HN-3,3′-Co(1,2-C2B9H10)(1′,2′-C2B9H11)] were determined by single crystal X-ray diffraction.

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