Freeman, Fillmore published the artcileReaction of aminopropanedinitrile 4-methylbenzenesulfonate [aminomalononitrile p-toluenesulfonate (tosylate)] with aromatic aldehydes, SDS of cas: 5098-14-6, the publication is Journal of Organic Chemistry (1991), 56(2), 657-63, database is CAplus.
(NC)2CHNH2·HO3SC6H4Me-4 reacts with aromatic aldehydes in NaOAc-MeOH to give diastereoselectively (E,E)-RCH:NC(CN):C(NH2)OMe (R = C6H4R1-4, R1 = OMe, OEt, OAc, H, Br, NO2, CO2Me; R = 3-pyridyl, 3-thienyl) and trans-3,6-diaryl-2,2,5,5-tetracyanopiperazines I (same R). The product distribution depends on the ratio of reactants and the structures of the substrates. Electron-releasing groups on the 4-position of the Ph ring favor piperazine formation. The formation of piperazines may involve synthetically useful N-protonated aryl- and cyano-stabilized azomethine ylide (prototropic 1,3-dipoles) intermediates which could have resulted from an imine-azomethine ylide tautomerism of prior formed 1-aryl-3,3-dicyano-2-aza-1-propenes. [4+2]-1,3-Dipolar cycloaddition reactions of the highly reactive azomethine ylides with MeO2CCCCO2Me give 3,4-dicarbomethoxy-2-cyano-5-aryl-3-pyrrolines, which undergo facile dehydrocyanation to 3,4-dicarbomethoxy-2-cyano-5-arylpyrroles. The possible intermediacy of ketenimines and of aryl- and cyano-stabilized 2-azaallyl anionic intermediates in equilibrium with azomethine ylides is also considered.
Journal of Organic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, SDS of cas: 5098-14-6.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts