A new simple approach to the preparation of imidazo [4,5-e]-1,2,4-triazine derivatives

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

“…The starting compound 2 is readily accessible and can be synthesized from 4,5-dihydroxy-4,5-diphenylimidazolidine-2-one [42] and thiosemicarbazide in 96% yield [43]. …”

Syntheses of imidazo[4,5-e]-1,2,4-triazines via the reaction of 1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one with aminoguanidine and semicarbazide

“…5,6 However, aminoguanidine introduced into the reaction with DHI led to 4,5-bis(aminoguanidino)imidazolidin-2-ones 1 and 4-(guanidinoimino)imidazolidin-2-ones 2 rather than to imidazo[4,5-e]-1,2,4-triazines. [6][7][8] Published data on the interaction between DHI and semicarbazide are unavailable.…”

“…§ According to its results, the geometry of the cationic moiety of † Clophelinum -hydrochloride of N- (2,6- 5a (Figure 1) is very similar to that in its analogue with 5,7-dimethyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones. 5 The conformation of the imidazole cycle is twist; the N(1) and N(2) atoms deviate from the plane of the three carbons by 0.37(1) and -0.32(1) Å, respectively. The conformation of the triazine moiety can also be described as twist.…”

Glycolurils in α-ureido-and α-aminoalkylation reactions 1. α-Ureidoalkylation of sulfamides with N-(hydroxymethyl)glycolurils

“…Based on the results obtained, we have developed general methods for the targeted synthesis of various N substituted glycolurils (2,4,6,8 tetraazabicyclo[3.3.0] octane 3,7 diones) 1 (including hydroxy(carboxy)alkyl ated ones) 1,5,6 and 3 thioxoperhydroimidazo[4,5 e] [1,2,4]triazin 6 ones 2. 3,4 In addition, we have discov ered novel reactions leading to 4,5 bis(3 alkylureido , thiosemicarbazido , and 3 aminoguanidino)imidazolidin 2 ones 3-5 and 1,3 dialkyl 4 guanidinoiminoimid azolidin 2 ones 6. 3,4 Out of N (hydroxymethyl)glycolurils, only 2,4,6,8 tet rakis(hydroxymethyl)glycolurils have been used hitherto as ureidoalkylating reagents (in the synthesis of cucur biturils).…”

“…3,4 In addition, we have discov ered novel reactions leading to 4,5 bis(3 alkylureido , thiosemicarbazido , and 3 aminoguanidino)imidazolidin 2 ones 3-5 and 1,3 dialkyl 4 guanidinoiminoimid azolidin 2 ones 6. 3,4 Out of N (hydroxymethyl)glycolurils, only 2,4,6,8 tet rakis(hydroxymethyl)glycolurils have been used hitherto as ureidoalkylating reagents (in the synthesis of cucur biturils). 7, 8 Because glycolurils belong to a novel class of neuro tropic compounds 9-11 and exhibit other types of bio logical activity, 12, 13 it was of practical interest to de sign a molecule combining the glycoluril fragment and other pharmacophore (e.g., sulfamide 14 ) groups.…”