Cyanuric acid derivatives

Methyl anthranilate condensed with 646 to give 2-phenyl-4-imino-l,3, 5-triazino[2,l-6]quinazolin-6-one (647) [69JCS(D)1040]. Condensation of the cyanuric acid derivative 648 with methyl anthranilate gave 649 which, upon cyclization, afforded a mixture of the two isomeric 4(2)-ani-lino-4(2)-hydroxy-l,3,5-triazino[2,l- ]quinazolin-6-ones (650 and 651) (75USP3887554). 

Figure 10.51 Melamine-cyanuric acid derivatives arranged according to their relative stability as measured by the HBI(N — 1) parameter. (Reprinted with permission from Section Key Reference 1995 American Chemical Society).

N. Kimizuka, T. Kawasaki, K. Hirata, T. Kunitake, Supramolecular Membranes. Spontaneous Assembly of Aqueous BUayer Membrane via Formation of Hydrogen Bonded Pairs of Melamine and Cyanuric Acid Derivatives ,]. Am. Chem. Soc., 120,4094 (1998)... 

A -alkyl-2,4-dioxohexahydro-l,3,5-triazines 33 were oxidized easily with oxygen to the corresponding cyanuric acid derivatives 34 <06M185>. 

Properties White, crystalline powder. The ketone isomer of cyanuric acid. Derivatives of isocyanuric acid, such as dichloro- and trichloroisocyanuric acid and potassium and sodium dichloroisocyanurate, are bleaches and sanitizers. 

Rgure20 Folding of a molecular strand (bottom) induced by the binding of a cyanuric acid-derived template, generates different possible conformers (top) and leads to the formation of fibers from the helical conformer (top right). 

Kimizuka and coworkers have extended their own work, to the assembly of bilayer membranes. For example, multiple hydrogen-bonding interactions between 57 and cyanuric acid derivative 59 containing a polar head group leads to hydrogen-bonded tapes that organize into bilayers [115,116]. The proposed supramolecular structure of the bilayer, represented schematically in Figure 34, was verified by IR and x-ray diffraction studies of films cast from an aqueous dispersion of the bilayer, as well as by electron microscopy of the dispersions. 

Figure 5 Possible complementary hydrogen-bond networks formed from melamine and cyanuric acid derivatives, (a) Linear tape, (b) crinkled tape, and (c) circular rosette.

Melamine (2,4,6-triamino-l,3,5-triazine) is a relatively non-toxic compound with acute toxicity observed in rodents, with oral lethal doses (LD50) of 3100 mg kg and 3900 mg kg in male rats and male mice, respectively." In another study, a 125 mg kg oral dose of melamine showed only diuretic effects in dogs." Toxicity studies of cyanuric acid derivatives (e.g. sodium cyanurate) at 700 mg kg and 2200 mg kg doses in rats and mice, respectively, resulted in bladder calculi and bladder epithelial hyperplasia, with no other adverse effects." In other studies, it was observed that dietary monosodium cyanurate administered in dogs for 6 months at 0.8% concentration produced no adverse effects, although at 8% for a longer period of 16 to 24 months it produced kidney fibrosis and fical dilation. This was attributed to the low solubility of sodium cyanurate, due to which it precipitated at higher concentrations in urine, leading to renal dysfunction." ... 

Cyanuric chloride is prepared by chlorinating hydrocyanic acid at 20 - 40 °C in aqueous medium, and after drying, trimerizing to cyanuric acid.The most important cyanuric acid derivates are the aminotriazines, which are used as pesticides, especially as herbicides [335],... 

Enghn M, Makarov S, Dubov S, Yakubovich A (1965) Fluorination of cyanuric acid derivatives. Zhurnal Obshchei Khimii 35 1416-1420... 

The use of molecular recognition was also extended to silylated melamine or cyanuric acid derivatives that formed complexes through hydrogen bonding [62]. 

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