2,3-Dicyano-5,7-bismethylthieno[3,4-b]pyrazine (5), has been obtained as a minor product from reactions of S-nucleophiles with 5,6-di(1-bromoethyl)pyrazine-2,3-dicarbonitrile (3), or from a condensation of 4-hydroxy-2,5-dimethyl-2,3-dihydrothiophen-3-one (4) with diaminomaleonitrile. The molecular structure of compound 5 has been confirmed by X-ray diffraction. A partial separation of charge ca...

We have judiciously constructed a novel ICT-based ratiometric OCl(-) probe capable of ratiometric imaging in the live cells based on the new OCl(-)-promoted de-diaminomaleonitrile reaction.

Condensation of 5,6-diamino-4,7-phenanthroline with glyoxal provides 1,4,5,12-tetraazatriphenylene in quantitative yield. This procedure avoids the 50% loss of product inherent in previous methods. Derivatives were also prepared by using alpha-dicarbonyl compounds other than glyoxal. Additional derivatives were prepared from 1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile, produced by condensa...

A new pyrene derivative (1) containing a diaminomaleonitrile moiety exhibits high selectivity for Cu2þ detection. Significant fluorescence enhancement was observed with chemosensor 1 in the presence of Cu2þ. However, the metal ions Agþ, Ca2þ, Cd2þ, Co2þ, Fe2þ, Fe3þ, Hg2þ, Mg2þ, Mn2þ, Ni2þ, Pb2þ, and Zn2þ produced only minor changes in fluorescence values for the system. The apparent association...

Diaminomaleonitrile (DAMN, 2,3-diamino-cis-2butenedinitrile) with the formula (H2N)(NC)C=C(CN)(NH2) appears to be symmetric and has been known as an unsaturated electron rich ligand as well as a tetramer of hydrogen cyanide, resulting from the polymerization of HCN under basic conditions 1 . The reaction of DAMN with aromatic aldehydes is very interesting as in every case 1+1 condensed Schiff b...

The first metalated porphyrazinediols 11 have been prepared from (L)-(+)-dimethyl tartrate via conversion into the corresponding dispoke or 2,3-dimethoxy-2,3-butanediyl protected 2,3-dihydroxymaleonitrile, Linstead macrocyclization, transmetalation, and deprotection. Their stability is very dependent on the nature of the metal ion in the cavity of the porphyrazine. Reaction of these porphyrazin...

ABSTRACT An earlier developed alkylating path leading to tetraalkylated diaminomaleonitrile derivatives was explored. Attempts to explain the reactivity of the representative dialkylated diaminomaleonitrile 2,3-bis[(3-pyridylmethyl)amino]-2(Z)-butene-1,4-dinitrile during the alkylation reaction were performed using X-ray and density functional theory (DFT) studies. The condensed Fukui functions...

The reaction between diaminomaleonitrile (DAMN) and aldehydes and the resulting monoimines are well known. Since the standard reaction conditions involve the use of toxic solvents (typically methanol), we have sought to apply green chemistry principles to this reaction by either using water as the solvent without any catalysts or employing "solvent-free" conditions. The monoimines derived from ...