Pyrazine

Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C₄H₄N₂.

Pyrazine is a symmetrical molecule with point group D2h.Derivatives like phenazine are well known for their antitumor, antibiotic and diuretic activity. Pyrazine is less basic in nature than pyridine, pyridazine and pyrimidine. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human polymorphonuclear leukocytesLife Sciences, 2003, 72, 2465-2472, DOI: http://dx.doi.org/10.1016/S0024-3205(03)00139-5. Tetramethylpyrazine is also a component of some herbs in traditional Chinese medicine.

Synthesis

Many methods exist for the organic synthesis of pyrazine and derivatives and some of them very old.

In the Staedel-Rugheimer pyrazine synthesis (1876) 2-chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to a pyrazine Ueber die Einwirkung von Ammoniak auf Chloracetylbenzol (p 563-564) W. Staedel, L. Rügheimer Berichte der deutschen chemischen Gesellschaft Volume 9, Issue 1 , Pages 563 - 564 1876 A variation is the Gutknecht pyrazine synthesis (1879) also based on this selfcondensation but differing in the way the alpha-ketoamine is synthesised (the chlorine compound in the above method is a......
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