Fundamental Studies on the Structures and Spectroscopic Properties of Imidazo[1,2-<i>a</i>]pyrazin-3(7<i>H</i>)-one Derivatives

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  • Nakai Shunichiro
    Department of Applied Physics and Chemistry, The University of Electro-Communications
  • Yasui Masanori
    Department of Applied Physics and Chemistry, The University of Electro-Communications
  • Nakazato Masaki
    Center for Instrumental Analysis, The University of Electro-Communications
  • Iwasaki Fujiko
    Department of Applied Physics and Chemistry, The University of Electro-Communications
  • Maki Shojiro
    Department of Applied Physics and Chemistry, The University of Electro-Communications
  • Niwa Haruki
    Department of Applied Physics and Chemistry, The University of Electro-Communications
  • Ohashi Mamoru
    Department of Materials Science, Kanagawa University
  • Hirano Takashi
    Department of Applied Physics and Chemistry, The University of Electro-Communications

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  • Fundamental Studies on the Structures and Spectroscopic Properties of Imidazo[1,2-a]pyrazin-3(7H)-one Derivatives

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The fundamental physical properties of 2-methyl and 2-phenylimidazo[1,2-a]pyrazin-3(7H)-one 1 and 2, and their N- and O-alkylated derivatives 3–6 have been investigated by X-ray crystallography, UV/vis absorption spectroscopy, NMR, and AM1-COSMO calculations. The crystal structures of 3 and 4 showed that the imidazo[1,2-a]pyrazin-3(7H)-one (imidazopyrazinone) π-system has a planar ring structure and a weakened carbonyl character of the C3–O10 bond, suggesting that the imidazopyrazinone π-system has the character of a zwitter-ionic resonance structure to increase the aromaticity. The data concerning the bond length alternations and the NMR chemical shifts of 1–4 also support that their imidazopyrazinone rings have small portions of aromatic character. In addition, imidazopyrazinone derivatives 1–4 showed solvatochromism originating by hydrogen-bonding interactions with hydrogen-bond donor solvent molecules; derivatives 1 and 2 prefer to be the NH form isomers in their tautomeric equilibriums. These observations were consistently evaluated by MO calculations. The physical properties of protonated species of 1–6 and anion species of 1 and 2 were also established. The fundamental properties of the imidazopyrazinone π-system explain the several problems of the chemi- and bioluminescence reactivities of imidazopyrazinone derivatives and of the construction of a bioluminescent supramolecule.

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