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Pyrazine
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<h2 id="synthesis">Synthesis</h2> <p>Many methods exist for the <a href="/facts/Organic_synthesis/aprl6Iq7">organic synthesis</a> of pyrazine and its derivatives. Some of these are among the oldest synthesis reactions still in use. </p><p>In the Staedel–Rugheimer pyrazine synthesis (1876), <a href="/facts/2-Chloroacetophenone/SXmG7eHu">2-chloroacetophenone</a> is reacted with <a href="/facts/Ammonia/MtLtJFtz">ammonia</a> to the amino ketone, then condensed and then oxidized to a pyrazine.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> A variation is the Gutknecht pyrazine synthesis (1879) also based on this <a href="/facts/Selfcondensation/wMG0F6La">selfcondensation</a>, but differing in the way the alpha-ketoamine is synthesised.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a><a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <p>The Gastaldi synthesis (1921) is another variation:<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a><a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Alkylpyrazine/oxQSdBeE">Alkylpyrazines</a></li> <li><a href="/facts/Methoxypyrazines/elV8mt3j">Methoxypyrazines</a></li> <li><a href="/facts/Simple_aromatic_ring/dftWcLcL">Simple aromatic rings</a></li> <li><a href="/facts/Benzene/Fguue7nr">Benzene</a>, an analog without the nitrogen atoms</li> <li><a href="/facts/Pyridazine/jLflt9M1">Pyridazine</a>, an analog with the second nitrogen atom in position 2</li> <li><a href="/facts/Pyridine/X817hCch">Pyridine</a>, an analog with only one nitrogen atom</li> <li><a href="/facts/Pyrimidine/uFRSB8Cq">Pyrimidine</a>, an analog with the second <a href="/facts/Nitrogen/Nf1QpGDz">nitrogen</a> <a href="/facts/Atom/FoQ4kGN5">atom</a> in position 3</li> <li><a href="/facts/Piperazine/hAwqCDRo">Piperazine</a>, the saturated analog</li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="http://www.inchem.org/documents/jecfa/jecmono/v48je12.htm">Safety evaluation of food additives – pyrazine derivatives</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>"Pyrazine | C4H4N2 | ChemSpider". www.chemspider.com. Retrieved 4 January 2022. <a href="https://www.chemspider.com/Chemical-Structure.8904.html?rid=e2532a2c-d5cb-457e-884b-ca9e4c8bd96b" target="_blank">https://www.chemspider.com/Chemical-Structure.8904.html?rid=e2532a2c-d5cb-457e-884b-ca9e4c8bd96b</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Zhang, Zhaohui; Wei, Taotao; Hou, Jingwu; Li, Gengshan; Yu, Shaozu; Xin, Wenjuan (2003). "Tetramethylpyrazine scavenges superoxide anion and decreases nitric oxide production in human polymorphonuclear leukocytes". Life Sciences. 72 (22): 2465–2472. doi:10.1016/S0024-3205(03)00139-5. PMID 12650854. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Staedel, W.; Rügheimer, L. (1876). "Ueber die Einwirkung von Ammoniak auf Chloracetylbenzol". Berichte der Deutschen Chemischen Gesellschaft. 9: 563–564. doi:10.1002/cber.187600901174. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>"Ueber Nitrosoäthylmethylketon". Berichte der Deutschen Chemischen Gesellschaft. 12 (2): 2290–2292. 1879. doi:10.1002/cber.187901202284. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01421-2 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>G. Gastaldi, Gazz. Chim. Ital. 51, (1921) 233 <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Amines: Synthesis, Properties and Applications Stephen A. Lawrence 2004 Cambridge University Press ISBN 0-521-78284-8 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> </ol>