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1、l,4-Diformyl-2,3,5,6-tetrahydroxypiperazine. Formamide (135 g, 119 ml, 3.0 mol) was added to stirred aqueous glyoxal (40% w/w, 435 g, 3.0 mol), and the pH was adjusted to 8.5 by using aqueous sodium hydroxide solution (10 M). The temperature rose slowly to 30°C over the first 30 min, and the solution developed a yellow tinge. The exotherm subsided, and after 4 h of stirring, the mixture was left to stand for 3 days. A first crop of the product (93 g) was collected by filtration, and a second crop was obtained by adjusting the pH of the filtrate to 9, the temperature of the mixture being controlled at 25°C with ice/water and the additional product being collected after 5 h. Both crops were washed well with water, dried, and purified by digesting the solid twice in a hot mixture of dimethylformamide/water (80:20). This involved using 70 ml of this mixture for each 30 g of solid, maintaining the stirred slurry at 75°C for 30 min, then cooling it to 30°C, collecting the solid, and washing it well with water. The product was dried over a desiccant to give a white solid (204 g, 66%), which darkened substantially above 190 °C and decomposed above 210°C (lit. mp ca. 225°C dec).