Practical synthesis of bis-substituted tetrazines with two pendant 2-pyrrolyl or 2-thienyl groups, precursors of new conjugated polymers

Novel linear oligoheterocycles based on substituted tetrazines are described. The desired compounds have been accomplished by a variation of the original Pinner [Ann. Chem., 297 (1897) 221] synthesis in which the aromatic nitrile reacted with hydrazine in an aqueous solution to give bis(pyrrolyl)tet...

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Bibliographic Details
Published in:Tetrahedron 2003-06, Vol.59 (26), p.4761-4766
Main Authors: Sołoducho, Jadwiga, Doskocz, Jacek, Cabaj, Joanna, Roszak, Szczepan
Format: Article
Language:English
Subjects:
bis-dioxanethiophene
bis-thiophene
precursors
tetrazines
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Summary:Novel linear oligoheterocycles based on substituted tetrazines are described. The desired compounds have been accomplished by a variation of the original Pinner [Ann. Chem., 297 (1897) 221] synthesis in which the aromatic nitrile reacted with hydrazine in an aqueous solution to give bis(pyrrolyl)tetrazines or bis(phenyl)tetrazines. The bis(phenyl)tetrazines reacted with 3,4-ethylenedioxy-2-(trimethyltin)thiophene or 2-(trimethyltin)thiophene in the presence of Pd(PPh 3) 2Cl 2 or Pd(PPh 3) 4 as catalyst to give the desired compounds. Quantum-chemical calculations were performed to assess the usefulness of the synthesized compounds for electropolymerization. Studies have indicated qualitative difference between bis-pyrrole tetrazine and bis-phenyl tetrazines regarding the electronic density rearrangement due to the loss of an electron. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00709-9