Malononitrile dimerization

Zemer MC, Reidlinger C, Fabian WMF, Junek H (2001) Push-dyes containing malononitrile dimer as acceptor synthesis, spectroscopy and quantum chemical calculations. J Mol Struct THEOCHEM 543(1-3) 129-146... 

Methanal, f31 Methanoic acid, f36 Methenamine, h49 Malononitrile dimer, a267 Methone, d596... 

The 4-aminopyridine derivative 92, prepared from the reaction of ethyl benzoylacetate and malononitrile dimer 91, undergoes the coupling reaction with aromatic diazonium salts to afford azo derivatives such as 93. Under refluxing conditions in ethanolic sodium hydroxide, these azo compounds cyclize to pyrido[3,2-f]pyridazines and pyrido[3,2-r]-pyridazino[2, 3 - ]quinazolines (Scheme 15) <2005AP329>. 

The cyclization of malononitrile and malononitrile dimer (134) by hydrogen bromide was examined by R. A. Carboni et al.,102 who obtained 2-bromo-3(or 5)-cyano-2,4-diaminopyridine. This, in view... 

The reaction of oxiranes with the sodium salt of malononitrile dimer gives rise to bicyclic compounds, for example, dihydrofuropyridines (Eq. 217). ... 

A noteworthy procedure for the synthesis of annulated 1,6-naphthyridines also uses a three-component condensation of the malononitrile dimer, salicylaldehyde and acetone giving rise to 1,6-naphthyridines 92 (1988JCS(P1)2053). 

Aryl hydrazones of benzoylacetonitrile are reported to react with 2-aminoprop-l-ene-l,l,3-tri-carbonitrilc ( malononitrile dimer ) in the presence of ammonium acetate to give 5-amino-l-aryl-7-imino-4-phenyl-1,7-dihydropyndo[2,3-c]pyridazine-3,6-dicai bonitriles in 50-59% yield.29,150... 

Aminoprop-l-ene-l,l,3-tricarbonitrile ( malononitrile dimer ) condenses with mesoxalo-dinitrile arylhydrazones to give 2,4-diamioo-6-aryl-5-imino-5,6-dihydropyrido[2,3-(/]pyridazine-3,8-dicarbonitriles l.29... 

Malononitrile dimer (147) reacted with dimethylformamide dimethyl acetal 210 to yield 211, which was cyclized with amines to give aminopyridines 212 k 148, a mixed dimer prepared from 10 and ethyl cyanoacetate, was cyclized in acidic or basic media to afford cyanopyridones 213 (X = Cl, Br, OMe, OEt, OH). Reacting 147 with excess 210 gave the product 214, which was cyclized with ammonia to yield 215. ... 

Condensing 239 with malononitrile afforded the polycyclic pyridazine derivative 243 where malononitrile dimerized into 194a prior to its condensation with 239 (1995T12745 Scheme 43). 

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