Pirazina

Pirazina
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Nome IUPAC Pyrazine
Outros nomes 1,4-Diazabenzeno, p-Diazina, 1,4-Diazina, Paradiazina, Piazina, UN 1325
Identificadores
Número CAS 290-37-9
PubChem 9261
Número EINECS 206-027-6
ChEBI 30953
SMILES
InChI
1/C4H4N2/c1-2-6-4-3-5-1/h1-4H
Propriedades
Fórmula molecular C4H4N2
Massa molar 80,09 g/mol
Aparência cristais brancos
Densidade 1,031 g/cm3
Ponto de fusão

52 °C

Ponto de ebulição

115 °C

Solubilidade em água Solúvel
Riscos associados
NFPA 704
2
2
0
 
Frases R R11, R36/37/38
Frases S S16, S26, S36
Ponto de fulgor 55 °C c.c.
Compostos relacionados
Compostos heterocíclicos relacionados Piridina (apenas um N no anel)
Pirimidina (1,3-diazina)
Piridazina (1,2-diazina)
Tetrazina (quatro Nsn no anel, instável)
Piperazina (saturado)
Compostos relacionados Pteridina (fusão com pirimidina)
Fenazina (dibenzo-p-diazina)
Ácido pirazinoico
Página de dados suplementares
Estrutura e propriedades n, εr, etc.
Dados termodinâmicos Phase behaviour
Solid, liquid, gas
Dados espectrais UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão
Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

Pirazina é um composto orgânico heterocíclico e aromático com a fórmula C4H4N2. Pirazina é uma molécula simétrica com grupo pontual de simetria D2h. É encontrada no ácido fólico na forma de pterina. Derivados tais como fenazina são bem conhecidas pelas suas atividades antitumores, antibióticas e diuréticas. Pirazina é menos básica em natureza que a piridina, piridazina e pirimidina. Tetrametilpirazina (também conhecida como ligustrazina) é descrita como eliminando o ânion superóxido e diminuindo a produção de óxido nítrico em leucócitos polimorfonucleares em humanos,[1] e é um componente de algumas ervas na medicina tradicional chinesa.[2]

Síntese

Existem numerosos métodos para o síntese orgânica da pirazina e de seus derivados. Algumas delas estão entre as mais antigas reações de síntese ainda em uso.

Na síntese da pirazina de Staedel–Rugheimer (1876) 2-cloroacetofenona reage com amônia à aminocetona, então condensada e oxidada à pirazina.[3] Uma variação é a síntese de pirazina de Gutknecht (1879) também baseada sobre esta autocondensação, mas diferindo na rota pela qual a alfa-cetoamina é sintetizada. [4][5]

Síntese de pirazina de Gutknecht

A síntese de Gastaldi (1921) é outra variação:[6][7]

Gastaldi synthesis

Referências

  1. ↑ Life Sciences, 2003, 72, 2465–2472, DOI: http://dx.doi.org/10.1016/S0024-3205(03)00139-5
  2. ↑ [1] - www.itmonline.org
  3. ↑ Ueber die Einwirkung von Ammoniak auf Chloracetylbenzol (pp. 563–564) W. Staedel, L. Rügheimer doi:10.1002/cber.187600901174 Berichte der deutschen chemischen Gesellschaft Volume 9, Issue 1, pp. 563–564, 1876
  4. ↑ Mittheilungen Ueber Nitrosoäthylmethylketon H. Gutknecht Berichte der deutschen chemischen Gesellschaft Volume 12, Issue 2 , pp. 2290–2292, 1879 doi:10.1002/cber.187901202284
  5. ↑ Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01421-2
  6. ↑ G. Gastaldi, Gazz. Chim. Ital. 51, (1921) 233
  7. ↑ Amines: Synthesis, Properties and Applications Stephen A. Lawrence 2004 Cambridge University Press ISBN 0-521-78284-8

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