Crystal properties of N-alkyl-substituted glycolurils as the precursors of chiral drugs

Absolute Asymmetric Synthesis of Stereochemically Labile Aldehyde Helicates and Subsequent Chirality Transfer Reactions

“…Isolation of new conglomerates: The crystal structure of [Al-(OC 6 H 3 Ph 2 ) 3 PhCHO] (2), which has previously been deposited with the Cambridge Structural Database, [15] is based on a conglomerate that crystallizes in the P2 1 space group. This crystal structure was determined by using Mo Ka radiation, and the asymmetric unit contains one molecule with the following unit cell dimensions: a = 10.731, b = 20.441, c = 10.908 , b = 99.758.…”

“…However, on closer inspection it became evident that some ATPH complexes could be less suitable for this purpose than others since the substrate can adopt several different orientations in the chiral pocket. The asymmetric unit in [Al(OC 6 H 3 Ph 2 ) 3 PhCH=CHCHO] (1) (Scheme 3) consists of three molecules, each with a different orientation of the cinnamaldehyde ligand. Hence the preparation of new ATPHaldehyde complexes was a logical starting point in the search for a conglomerate with an ordered substrate ligand.…”

Synthesis of first representatives of 3,3′-bi(6,8-dialkyl-2,4-dioxa-6,8-diazabicyclo[3.3.0]octan-7-ones)

“…In particular, they represent a novel class of neurotropic compounds [2,3,9,10]. The synthesis of glycolurils is based on the reaction of glyoxal or 4,5-dihydroxyimidazolidin-2-ones with N-nucleophiles containing urea fragments in the water or watermethanol at pH 1 [4][5][6][7]13,14].…”

“…For several years we have been interested in chemistry and stereochemistry of 2,4,6,8-tetraazabicyclo [3.3.0]octan-3,7-diones (glycolurils) [1][2][3][4][5][6][7][8][9], possessing a wide range of biological activity [9][10][11][12]. In particular, they represent a novel class of neurotropic compounds [2,3,9,10].…”

Synthesis of Pyrimidopyrimidinediones in a Deep Eutectic Reaction Mixture

“…[10] The drug mebicar, an analogue of glycoluril, is a tranquilizer whereas albicar shows antidepressant activity. [11] Similarly, pyrimidopyrimidine derivatives are an important class of annulated uracils of biological significance due to their close resemblance to purine and pteridine systems. Pyrimidopyrimidine derivatives show pharmacological activity as vascodilators, [12] as well as antiallergic, [12] antitumour [13] and antiviral [14] properties.…”