Synthesis of 2-amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine.
2-Amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine (2), a precursor of Watasenia preluciferin (coelenterazine) (1), is widely distributed in marine bioluminescent animals. It was prepared from p-hydroxyphenylglyoxal aldoxime (5) in two steps; by condensation with or-aminophenylpropiononitrile in the presence of TiCl4 in pyridine, followed by reduction of the resulting N-oxide (6) with Zn-AcOH in CH2Cl2 and produced 2, with an 89% overall yield. This procedure was linked with the facile one-step preluciferin synthesis reported in the previous paper. Thus, Watasenia preluciferin (1), frequently required for various chemiluminescent and bioluminescent studies, was coveniently synthesized in three steps from 5, with a 56% overall yield, overcoming the difficulty of obtaining it from natural sources.
Kakoi
Hisae
H
Faculty of Pharmacy, Meijo University, Nagoya, Japan. kakoi@ccmfs.meijo-u.ac.jp
D007093:Imidazoles; D008163:Luminescent Measurements; D008968:Molecular Conformation; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
D007093:Imidazoles; D011719:Pyrazines; C017144:coelenterazine