Synthesis and properties of symm-triazines. 3. Reactions of 2-alkyl-4,6-bistrichloromethyl-symm-triazines containing higher alkyl groups with ammonia and aliphatic amines

Tautomerism in 5,8‐Diaza‐7,9‐dicarbaguanine (‘Alloguanine’)

“…This compound as well as its hydrolysis product 3 were prepared according to methodology described by Kelarev et al[17]. To a suspension of 1 (14.4 g, 0.1 mol) in 100 ml of DMF was added dropwise of Cl 3 CCN (28.8 g, 0.2 mol, 2 equiv.).…”

Mannich-Type C-Nucleosidations in the 5,8-Diaza-7,9-dicarba-purine Family1

“…The methods used for preparing purinoids 2 (Scheme ), 3 (Scheme ), and 4 (Scheme ) were chosen without recourse to the potentially etiological aspects that we associate with these nucleobase analogues. N -Formyl-glycyl-guanidine 5 , easily obtained from N -formyl-glycine ethylester and guanidine, reacts with trichloroacetonitrile to give the trichloromethyl-triazine derivative 6 , which, following the methodology described by Kelarev et al, is hydrolytically converted to 7 . Remarkably, as well as satisfyingly, when this N -formyl-aminomethyl-triazine is treated with concentrated H 2 SO 4 at 100 °C, a procedure reported in the literature for the cyclization of other keto-amino-triazine derivatives, dehydrative cyclization proceeds regioselectively and gives the guanine analogue 2 in high yield; the isomeric cyclization product is not observed…”