Hydrogen cyanide chemistry. VIII. New chemistry of diaminomaleonitrile. Heterocyclic synthesis

Abstract

Alkyl derivatives of diaminomaleonitrile (DAMN), are prepared by direct methylation and by reduction of Schiff bases. Cyclic anhydrides and DAMN produce amide acids. 2,3-Dicyanodiazepines and 2,3-dicyanodihydrodiazepines are prepared by condensation of DAMN with 1,3-diketones or other carbonyl derivatives. 2-Substituted 4,5-dicyanoimidazoles are prepared by improved cyclization procedures of Schiff bases and amides of DAMN. Tetrasubstituted pyrazines are prepared by condensation of DAMN with diimines prepared from alcohols and cyanogen.

Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach

“…IR, 1 H-NMR, 13 C-NMR spectral analysis and 2-D experiments allowed us to establish the structures of the momoimines 2a-2k. Compounds 2a,b,d-j have been previously described [3,7,11,18,19] and the physical properties determined during this work are in complete agreement with those reported. It is noteworthy that no complete spectroscopic data for compounds 2a and 2g were found in the literature, while compounds 2c and 2k have not been described previously, although preparation of 2k under acid catalysis and using DMSO as solvent was claimed in a patent [20].…”

“…It has been used as a precursor for producing nucleotides and for synthesising a wide variety of heterocyclic compounds [1] including purines [2,3], pyrimidines [4], pyrazines [5] (some which are widely employed in the fluorescent dye industry [6]), imidazoles [7], biphenylenes [8], porphyrazines (which have great potential in optical sensor technology [9]) and diimines that are used as catalysts [10]. The reaction of DAMN with aromatic aldehydes is widely known to produce monoimines [11].…”

Studies on Imidazole and Its Derivatives with Particular Emphasis on Their Chemical/biological Applications as Bioactive Molecules/Intermediated to Bioactive Molecule

“…First time imidazole was prepared in 1858. Now-a-days several methods of sythesis of imidazoles are available some of these are given below in Schemes 1-9 [20][21][22][23][24][25][26][27][28][29]. From alkene, carbon monoxide and ammonia [25].…”

Five‐Membered Heterocycles: 1,3‐Azoles

“…This approach has been applied to the synthesis of imidazoles having a range of substituents at the 1-and 5-positions. A methodology for the preparation of 2-substituted-4,5-dicyanoimidazoles is the reaction of DAMN (diaminomaleonitrile) with carbonyl compounds under oxidative conditions [49]. A more recent variation is the reaction of DAMN with anhydrides to afford b-aminoenamides that dehydrates to afford the imidazole nucleus [50].…”