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Pyrazine is a heterocyclic aromatic organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
.

Pyrazine is a symmetrical molecule with point group
Point group

In mathematics, a point group is a group of geometric symmetry leaving a point fixed....
 D2h. It is found in folic acid
Folic acid

Folic acid and Folate are forms of the water-soluble B vitamins. Vitamin B9 is essential to numerous bodily functions ranging from nucleotide synthesis to the remethylation of homocysteine....
 in the form of pterin
Pterin

Pterin is a heterocycle compound composed of a pyrazine ring and a pyrimidine ring ; the pyrimidine ring has a carbonyl oxygen and an amino group....
. Derivatives like Phenazine
Phenazine

Phenazine , also called azophenylene, dibenzo-p-diazine, dibenzopyrazine, and acridizine, is a dibenzo annulation pyrazine and the parent substance of many dyestuffs, such as the eurhodines, toluylene red, indulines and safranines....
 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 leukocytes.






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Pyrazine is a heterocyclic aromatic organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
.

Pyrazine is a symmetrical molecule with point group
Point group

In mathematics, a point group is a group of geometric symmetry leaving a point fixed....
 D2h. It is found in folic acid
Folic acid

Folic acid and Folate are forms of the water-soluble B vitamins. Vitamin B9 is essential to numerous bodily functions ranging from nucleotide synthesis to the remethylation of homocysteine....
 in the form of pterin
Pterin

Pterin is a heterocycle compound composed of a pyrazine ring and a pyrimidine ring ; the pyrimidine ring has a carbonyl oxygen and an amino group....
. Derivatives like Phenazine
Phenazine

Phenazine , also called azophenylene, dibenzo-p-diazine, dibenzopyrazine, and acridizine, is a dibenzo annulation pyrazine and the parent substance of many dyestuffs, such as the eurhodines, toluylene red, indulines and safranines....
 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 leukocytes. Tetramethylpyrazine is also a component of some herbs in Traditional Chinese Medicine
Traditional Chinese medicine

Traditional Chinese medicine includes a range of traditional medicine practices originating in China. Although well accepted in the mainstream of medical care throughout East Asia, it is considered an alternative medicine system in much of the western world....
.

Synthesis

Many methods exist for the organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
 of pyrazine and derivatives and some of them very old.

In the Staedel-Rugheimer pyrazine synthesis (1876) 2-chloroacetophenone is reacted with ammonia
Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
 to the amino ketone, then condensed and then oxidized to a pyrazine 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 lachrymatory agent
Lachrymatory agent

A lachrymatory agent or lachrymator is a chemical compound that stimulates the corneal nerves in the eyes to cause tears, pain, and even temporary blindness....
)

The Gastaldi synthesis (1921) is another variation :


See also

  • Pyrimidine
    Pyrimidine

    Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring....
    , an analog with the second nitrogen
    Nitrogen

    Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
     atom
    Atom

    |-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
     in position 3.
  • Pyridazine
    Pyridazine

    Pyridazine is a heteroaromatic organic compound with the molecular formula C4H4N2, sometimes called 1,2-diazine....
    , an analog with the second nitrogen atom in position 2.
  • Pyridine
    Pyridine

    Pyridine is a simple and important heterocyclic aromatic organic compound with the formula CarbonHydrogenNitrogen. This colorless liquid with a distinctive fish-like odor is structurally related to benzene, wherein one CH group in the six-membered ring is replaced by a nitrogen atom....
    , an analog with only one nitrogen atom.
  • Benzene
    Benzene

    Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
    , an analog without the nitrogen atoms.
  • Simple aromatic ring
    Simple aromatic ring

    Simple aromatic rings, also known as simple arenes or simple aromatics, are aromatic organic compounds that consist only of a conjugated system planar ring system with delocalized_electron pi electron clouds....
    s
  • Methoxypyrazines
    Methoxypyrazines

    Methoxypyrazines are a class of chemical compounds that produce odors. The odors may be desirable, as in the case of certain wines, or undesirable, as in the case of the Asian Lady Beetle which produces isopropyl methoxy pyrazine ....


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