I will start this blog with a quite old but very interesting synthesis of pyrazine dicarboxylic acid.
This synthesis starts with the formation of quinoxaline, by the reaction of glyoxal and o-phenylendiamine in water with a 85-90% yield(1). Then the benzene fused ring is cleaved with a hot aqueous potassium permanganate solution (2), the mixture is cooled at room temperature and acidified with a 36% hydrochloric acid (3). The crude material is filtered off and recristallized in acetone to give the 2,3-pyrazinedicarboxylic acid with a 75-77% yield.
This synthesis starts with the formation of quinoxaline, by the reaction of glyoxal and o-phenylendiamine in water with a 85-90% yield(1). Then the benzene fused ring is cleaved with a hot aqueous potassium permanganate solution (2), the mixture is cooled at room temperature and acidified with a 36% hydrochloric acid (3). The crude material is filtered off and recristallized in acetone to give the 2,3-pyrazinedicarboxylic acid with a 75-77% yield.
Interestingly, this synthesis can be applied to quinolines, isoquinolines and naphtalenes to provide the corresponding dicarboxylic derivatives.
For more information:
2,3-PYRAZINEDICARBOXYLIC ACID
Organic Syntheses, Coll. Vol. 4, p.824 (1963); Vol. 30, p.86 (1950).
Reuben G. Jones and Keith C. McLaughlin.
1 commentaires:
It was extremely interesting for me to read this blog. Thank author for it. I like such themes and anything that is connected to them. I would like to read a bit more soon.
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