166985-87-1Relevant academic research and scientific papers
Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
supporting information, p. 197 - 209 (2015/03/03)
In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.
N-Substituted Glycine Derivatives: Prolyl Hydroxylase Inhibitors
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Page/Page column 43, (2008/12/06)
The invention described herein relates to certain pyrimidinedione N-substituted glycine derivatives of formula (I) which are antagonists of HIF prolyl hydroxylases and are useful for treating diseases benefiting from the inhibition of this enzyme, anemia being one example.
Oxidative rearrangement and cyclisation of N-substituted amidines using iodine(III) reagents and the influence of leaving group on mode of reaction
Ramsden, Christopher A.,Rose, Helen L.
, p. 2319 - 2327 (2007/10/03)
The products of reaction of N-substituted amidines 5 with hypervalent iodine reagents such as (diacetoxyiodo)benzene (DAIB), bis(trifluoroacetoxy)iodobenzene (BFIB) and [methoxy(tosyloxy)-iodo]benzene (MTIB) are determined by the reagent, the amidine substituents and the reaction temperature. C-Alkyl-N-arylamidines 5a-d cyclise in high yield giving benzimidazoles 6 but C,N-dialkyl- and C,N-diaryl-amidines 5e-l rearrange to give products derived from an intermediate carbodiimide. Use of N2-phenylfuran-2-carboximidamide 5j leads to N-(2-furyl)acetamide 15 in good yield, illustrating a convenient route to stable derivatives of highly unstable 2-aminofuran. The rearrangement of C,N-diarylamidines on reaction with DAIB contrasts with the observed formation of benzimidazole when the same precursors are treated with lead tetraacetate (LTA). Evidence is presented to support the view that the mode of reaction is determined by the nature of the leaving group in an imide intermediate 19: very good leaving groups [e.g. PhI, N2, AgCl and PhSO2O- (aq.)] appear to favour rearrangement whereas poorer leaving groups [e.g. Cl-, Me2S, Me3N and PhSO2O- (non-aq.)] favour cyclo-α-elimination.
