Synthesis and structure of aroylamidines and N-arylbenzamidines hydrochlorides

Abstract

Aroylamidines can be obtained as salts in a reaction of the corresponding arylcarbonitriles with anhydrous ethanol in the presence of dry HCl followed by treating intermediate imidoesters with alcoholic solution of ammonia. N-Arylbenzamidines are obtained by reacting benzonitrile with arylamines in the presence of AlCl 3 . The structure of arylamines and the reaction conditions signifi cantly affect the yield of the target product, and sometimes the very possibility of its preparation.

Transition‐Metal‐Free Approach to 4‐Ethynylpyrimidines via Alkenynones

“…para ‐Substituted arylamidines 7a – e were chosen as nucleophiles for the synthesis of pyrimidines by analogy with our previous results and were synthesized by a modified Pinner amidine synthesis protocol (Scheme ). In addition to the few literature procedures based on the treatment of nitriles with LiHMDS or dry HCl in ethanol,8,9 we have proven that basic conditions are more suitable for nitriles with electron‐withdrawing groups, whereas acidic conditions are preferable for nitriles with electron‐donating substituents (see the Exp. Sect.…”

C,N‐Diarylformamidines as Valuable Building Blocks in the Synthesis of Heterocyclic Compounds

“…In addition, it is worth paying attention to the ease of obtaining these reagents. The most common method for obtaining C,N-diarylformamidines 1 is the reaction of aniline and benzonitrile under the action of Lewis acid (Figure 1), [5] which makes it easy to vary substituents in benzene rings and, moreover, there are no problems with the availability of starting reagents.…”