Synthesis of 2-amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 2, 2002, Pages 301-302

  Kakoi, Hisae ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

2 aminopyrazine derivative; Bioluminescent compound; Precursor; Watasenia preluciferin

Indexed keywords

2 AMINO 3 BENZYL 5 (4 HYDROXYPHENYL)PYRAZINE; 4 HYDROXYPHENYLGLYOXAL ALDOXIME; ALDOXIME; ALPHA AMINOPHENYLPROPIONONITRILE; LUCIFERIN; NITRILE; OXIDE; PYRAZINE DERIVATIVE; PYRIDINE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE; COELENTERAZINE; IMIDAZOLE DERIVATIVE;

ARTICLE; BIOLUMINESCENCE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMOLUMINESCENCE; CONTROLLED STUDY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CHEMISTRY; CONFORMATION; LUMINESCENCE; METABOLISM;

IMIDAZOLES; LUMINESCENT MEASUREMENTS; MOLECULAR CONFORMATION; PYRAZINES;

EID: 0036482179     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.301     Document Type: Article

References (16)

1. Inoue S., Sugiura S., Kakoi H., Hashizume K., Goto T., Iio H., Chem. Lett., 1975, 141-144.
2. a) Shimomura O., Inoue S., Johnson F. H., Haneda Y., Comp. Biochem. Physiol., 65B, 435-437 (1980), and references therein;
3. b) Inoue S., Kakoi H., Okada K., Tanino H., Goto T., Agric. Biol. Chem., 47, 635-636 (1983), and references therein;
4. c) Inoue S., Kakoi H., Goto T., Chem. Comm., 1976, 1056-1057;
5. d) Inoue S., Kakoi H., Murata M., Goto T., Shimomura O., Chem. Lett., 1979, 249-252, and references therein;
6. e) Inoue S., Okada K., Tanino H., Kakoi H., Chem. Lett., 1987, 417-418.
7. Shimomura O., Johnson F. H., Biochemistry, 11, 1602-1608 (1972).
8. Kishi Y., Tanino H., Goto T., Tetrahedron Lett., 27, 2747-2748 (1972). Overall yield of 2 from 3 in three steps was 57.6%.
9. Kakoi H., Inoue S., Heterocycles, 48, 1669-1672 (1998).
10. Karg E., Arch. Pharm., 282, 49-56 (1944).
11. Freifelder M., Hasbrouck R. B., J. Am. Chem. Soc., 82, 696-698 (1960).
12. a) Keenan M., Jones K., Hibbert F., Chem. Comm., 1997, 323-324;
13. b) Chen F. Q., Gomi Y., Hirano T., Ohashi M., Ohmiya Y., Tsuji F. I., J. Chem. Soc. Perkin Trans. 1, 1992, 1607-1611;
14. c) Usami K., Isobe M., Tetrahedron, 52, 12061-12090 (1996);
15. d) Saito R., Hirano T., Niwa H., Ohashi M., J. Chem. Soc. Perkin Trans. 2, 1997, 1711-1716.
16. 5) That is, a mixture of 2 and excess p-hydroxyphenylpyruvic acid (7 equiv.) was heated in dioxane at 130°C under gentle refluxing. After 30 min, the solvent was then allowed to evaporate almost to dryness at 140°C. The resultant dark resinous residue was purified by chromatographic work to give 1 in 63% yield.