Pyridazine,oxazine, pyrrole,and pyrrolo[1,2‐a]quinazoline derivatives from malononitrile dimer

2‐Amino‐1,1,3‐tricyano‐3‐bromopropene was obtained from bromination of 2‐amino‐1,1,3‐tricyanopropene (malononitrile dimer) with N‐bromosuccinimide. This bromo derivative reacts with hydrazine hydrate, phenyl hydrazine, and hydroxylamine hydrochloride to afford pyridazine and oxazine derivatives, respectively. In base‐catalyzed reactions with primary aromatic amines and anthranilic acid derivatives, it produces N‐aryl pyrrol‐3,5‐dicarbonitrile and pyrrolo[1,2‐a]quinazolin‐5‐imine, or pyrrolo[1,2‐a]quinazolin‐5‐one derivatives, respectively. The structures of the newly synthesized heterocycles were established on the basis of elemental analyses and spectral data. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:612–616, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10199     

Phenylbiguanide as electron donor in heterocyclic synthesis

Phenylbiguanide reacts with some π-acceptors such as TCNE, TCNQ, CNIND, DCNQ, and CHL-o, if any. opy; 2003 Wiley Periodicals, Inc. Heteroatom Chem 15:63–66, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10213     

Organoiron polynorbornenes with pendent arylazo and hetarylazo dye moieties

Organoiron polynorbornene containing arylazo or hetarylazo dye chromophores has been prepared via ring opening metathesis polymerization using Grubbs' catalyst. The obtained polymers were isolated as brightly colored materials and displayed good solubility in polar organic solvents. The colors of these polymers were affected by the nature of the incorporated azo chromophores. Thermogravimetric analysis of these materials showed that the cleavage of the cyclopentadienyliron (CpFe⁺) moieties was between 225 and 231 °C, while the degradation of the polymer backbones occurred between 400 and 450 °C. UV-vis studies in DMF showed that the organoiron polymers containing arylazo dyes exhibit wavelength maxima around 425 nm. However, the replacement of these arylazo moieties with hetarylazo dyes displayed substantial bathochromic shifts in the λ_max values (≈ 511 nm).