ChemInform Abstract: A Facile Synthesis of 5‐Amino‐1‐aryl‐4‐cyanoimidazoles and 5‐Amino‐1‐ aryl‐4‐(cyanoformimidoyl)‐1H‐imidazoles from N‐Aryl‐N′‐(1,2‐ dicyanovinyl)formamidines

Abstract

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Imidazolylpyrrolone‐Based Small Molecules as Anticancer Agents for Renal Cell Carcinoma

“…The synthetic approach required the preparation of the intermediate 5‐amino‐4‐cyanoformimidoyl imidazoles 3 b – l , following a reaction sequence previously developed and optimized by the research group (Scheme 1 ). Imidate 1 , prepared from diaminomaleonitrile (DAMN) and triethyl orthoformate (TEOF) in the presence of mild acid catalysis (anilinium chloride) [14] was reacted with hydrazine [15] , anilines [16] and alkyl primary amines. [13] The reaction with hydrazine monohydrate occurred in dioxane leading to the isolation of amidrazone 2 a in 99 % yield.…”

“…The ethyl‐ N ‐(( Z )‐2‐amino‐1,2‐dicyanovinyl)‐formimidate 1 , the ( Z )‐ N ′‐(1‐amino‐2,2‐dicyanovinyl)‐ N ‐aryl/alkylformimidamide derivatives 2 and the 5‐amino‐1 H ‐imidazole‐4‐carbimidoyl cyanide derivatives 3 used in this work were prepared by previously described procedures. [ 13 , 14 , 15 , 16 ] The experimental procedures and characterization will only be presented for the new derivatives that were prepared in this work. Cyanoacetamides 7 were also prepared according to a previously described procedure.…”

“…The retrosynthetic approach proposed for the synthesis of compound 5 (Figure 3 ), shows that the reaction sequence can be initiated from imidate 1 , the precursor of amidine 2 . [ 13 , 14 , 15 , 16 ] Imidazole 3 , formed by intramolecular cyclization of 2 , is particularly reactive and carbon acids could already be incorporated in the cyanoformimidoyl substituent. [ 17 , 18 , 19 , 20 ] Compound 4 is expected from the reaction of 3 with cyanoacetamides leading to the desired product 5 by intramolecular cyclization.…”