Benzamidines Research Articles

Structure and Fluxional Behavior of Phenylmercury Derivatives of N,N'-Diarylform(benz)amidines

Activation barriers for fast 1,3-N,N' migrations of phenylmercury groups in the corresponding derivatives of N,N'-di(p-tolyl)form(benz)amidines have been calculated by density functional theory B3LYP/Gen, 6-311++G(d,p)/SDD to be ΔE ZPE ≠ = 4.5 and 3.0 kcal/mol. The results correspond to the data of dynamic NMR, which have shown the upper limit of activation barriers of these rearrangements (ΔG≠) to be below 8 kcal/mol. The calculations have shown that the most stable is the E-syn form of N-phenylmercury-N,N'-di(p-tolyl)form(benz)amidines stabilized by supplementary intramolecular coordination of mercury atom with imine nitrogen atom of the amidine triad.

Structure and fluxional behavior of phenylmercury derivatives of N,N’-diarylform(benz)amidines

Structure and fluxional behavior of phenylmercury derivatives of N,N’-diarylform(benz)amidines

Cyclocondensation of methyl 2-(5-methylisoxazol-3-yl)imino-3,3,3-trifluoropropionate with 1,3-binucleophiles

Cyclocondensation of methyl 2-(5-methylisoxazol-3-yl)imino-3,3,3-trifluoropropionate with 1,3-binucleophiles such as benzamidines, aminothiazoline, and 2-aminocrotonic acid nitrile results in trifluoromethyl-containing 3,5-dihydro-4-ones, 2,3-dihydro-6H-imidazo[2,1-b]thiazol-5-one, and 4,5-dihydro-1H-pyrrole-3-carbonitrile.

N'-acyl-N,N-(1,3,3-trimethylbicyclo [2.2.1]hept-2-ylidene)benzamidines with hypotensive activity.

The reaction of fenchone nitrimine (I) with benzamidine gave in good yield N,N-(1,3,3-trimethylbicyclo [2.2.1]hept-2-ylidene)benzamidine (II), which by acylation afforded N'-acyl-N,N-(1,3,3-trimethylbicyclo[2.2.1]hept-2-ylidene)benzam idines (III a-f) in excellent yields. Compounds (III) showed a moderate hypotensive activity in rats and a weak local anesthetic activity by infiltration in mice. Effects on heart rate and antiarrhythmic activity in rats are also reported.