Studies described in previous papers of this series (1-3) have shown that bisamides react readily with compounds possessing active H atoms. Thus, by the reaction of bisamides with ethyl nitroacetate, derivatives of ct-nitro-^-amino acids (1), with nitromethane a-nitro-|3-amino hydrocarbons (2), and with ethyl acetoacetate a-carbethoxy-/3-acetylamino-/3-arylethyl methyl ketones (3) are obtained. The reaction takes place in every case with one amide group of the bisamide, the other one remaining unchanged.In this paper wre report the results of our studies on the effect of ethyl cyanoacetate on bisamides. It wTas assumed that ethyl cyanoacetate would also react with bisamides in the same manner as the reagents mentioned, that is, to form compounds of formula I. However, instead of I, the products of the reaction wrere ß-aryl-a-cyanoacrylic acids (II). Probably the compounds I are formed in the 1307 SUMMARY When bisamides are reacted with ethyl eyanoacetate, one acetamido group is substituted by the eyanoacetate radical and the second acetamido group is split off, leading to the formation of /3-aryl derivatives of -cyanoacrylic esters.
When benzaldehyde, ethyl nitroacetate, and acetamide or ammonium acetate are allowed to react in the presence of acetic anhydride, a compound of m.p. 140-141°is formed in yields up to 63%. Its molecular formula is CuHibNüOí, indicating that it is formed from equimolecular amounts of benzaldehyde, acetamide, and ethyl nitroacetate by loss of one molecule of water.The same reaction occurs when using, instead of benzaldehyde, other aromatic aldehydes, such as veratraldehyde, acetylvanillin, piperonal, o-nitrobenzaldehyde and others. SUMMARY 1. By the reaction of a mixture of aromatic aldehydes, amides, and ethyl nitroacetate in acetic anhydride, or by the action of the nitro ester on bisamides in acetic anhydride, a new class of compounds is obtained, namely the derivatives of -nitro-jS-amino acids, in satisfactory yields.2. When heating esters of a-nitro-/3-acetylamino acids with solutions of alkali hydroxides, the following degradation products are formed: ammonia, acetic acid, hydrogen cyanide, and the acids corresponding to the aldehydes used for the synthesis.4 These bisamides are new compounds.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.