DAMN with Oxalyl Chloride

Compound 67 has also been prepared by (1) reaction of DAMN with oxalyl chloride (56LA95) and (2) by reaction of DISN with oxalyl chloride, followed by treatment with ethanethiol (72JOC4136). 

D. Condensation of DAMN with Oxalyl Chloride 1. 2,3-Dioxo-5,6-dicyano-l,2,3.4-tetrahydropyrazine... 

Bredereck and Schmotzer (1044), from diaminomaleonitrile (DAMN hydrogen cyanide tetramer) and oxalyl chloride, prepared 2,3-dicyano-5,6-dihydroxy-pyrazine but Stetten and Fox (1049) could not prepare 23-diamino-5-hydroxy-pyrazine from glycine amide and oxamide. Section 11.3 lists preparations from a, -diamino or a, -diimino compounds and reagents other than a,0-dicarbonyl compounds (384) with additional data (1050) and oxidation of 23-dichloro-quinoxaline with hot aqueous potassium permanganate gave 23-dicarboxy-5,6-dihydroxypyrazine (1051). 

---