Efficient method for the synthesis of 1,3-unsubstituted 2-imino-5-oxooctahydroimidazo[4,5-d]imidazolium iodides based on thioglycolurils

Synthesis and Structure of 1-Substituted Semithioglycolurils

“…Beige powder; yield: 0.22 g (51%) (approach 1); brown crystals; yield: 1.07 g (31%) (approach 2); mp 283-285 °С (MeOH) (283-285 °С (H 2 O) 6 ).…”

“…[2][3][4][5] Thio-, amino-, and sulfo-based analogues of glycolurils are less available. 2,6 More and more research has focused on semithioglycolurils I-IX (Figure 1), 2, including compounds I, II, V, VII, and VIII that were synthesized in our laboratory. 6,[12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] Although a wide range of trisubstituted semithioglycolurils I and II have been reported, they are still actively investigated, as some of them have antifungal and cytotoxic activities.…”

“…2,6 More and more research has focused on semithioglycolurils I-IX (Figure 1), 2, including compounds I, II, V, VII, and VIII that were synthesized in our laboratory. 6,[12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] Although a wide range of trisubstituted semithioglycolurils I and II have been reported, they are still actively investigated, as some of them have antifungal and cytotoxic activities. 12,13 Other compounds III-IX are represented by several examples and used as scaffolds in the synthesis of semithiobambusurils (III and VII), 11,27 in Claisen condensation matrices (IV), 10 and in the synthesis of tri-, tetra-, and polycyclic systems (V) [28][29][30][31] and iminoglycolurils (V, VII, VIII).…”

“…12,13 Other compounds III-IX are represented by several examples and used as scaffolds in the synthesis of semithiobambusurils (III and VII), 11,27 in Claisen condensation matrices (IV), 10 and in the synthesis of tri-, tetra-, and polycyclic systems (V) [28][29][30][31] and iminoglycolurils (V, VII, VIII). 6 Methods for the preparation of a small number of compounds III-IX reported in the literature are underdeveloped. The focus of this article is on a methodology for the synthesis of 1-substituted semithioglycolurils.…”

“…6,14,25 Compounds 1a,b were obtained by the reaction of 1-alkylureas 2a,b with 4,5-dimethoxyimidazolidine-2-thione (DMIT; 3) or 4,5-dihydroxyimidazolidine-2-thione (DHIT; 4) (approach 1). 6,25 Semithioglycoluril 1c was prepared by the condensation of 1-cyclohexyl-4,5-dihydroxyimidazolidin-2-one (5a) with KSCN and hydrochloric acid (approach 2). 14 Here, these approaches were studied in detail, and two methods for the synthesis of 1-substituted semithioglycolurils were developed.…”