Synthetic Methods for the Preparation of Triazepandiones and Review of their Applications

5-(3,4-Dimethoxybenzyl)-7-isopropyl-1,3,5-triazepane-2,6-dione acetonitrile solvate refined using a multipolar atom model

“…1. All bond distances and angles are normal (Table 1) and are in good agreement with the geometry of similar 1,3,5-triazepane-2,6-diones (Lena et al, 2006;Lena & Guichard, 2008). The S configuration of the C atom at the 2-position of the seven-membered ring was assumed from the precursor Boc-l-Tic OH compound.…”

“…The second half of the ring is composed of atoms C2/N1/C7/N6/C5 and only atom N6 is displaced from the mean plane, by 0.115 (2) Å ; for the other atoms, the deviation does not exceed 0.063 (2) Å . The dihedral angle between the two halves is 64.7 (1) and is almost in the range of values found for this group of compounds (57.74-63.93 ; Aubert et al, 2007;Lena et al, 2006;Lena & Guichard, 2008;Schaffner et al, 2006). The plane of the benzene ring makes angles of 82.1 (1) and 66.9 (1) with these planes, respectively.…”

“…1,3,5-Triazepane-2,6-diones are a novel class of dipeptidomimetics (Lena et al 2006;Lena & Guichard, 2008) whose skeleton can be readily prepared starting from N-protected dipeptides. All five points of diversity can be manipulated using either solution-phase or solid-phase synthesis.…”

A General Stereoselective Approach to 1,2,4-Triazepane-3-thiones/ones via Reduction or Reductive Alkylation of 2,4,5,6-Tetrahydro-3H-1,2,4-triazepine-3-thiones/ones

“…Development of efficient approaches to rare heterocyclic scaffolds is a fundamental challenge of organic synthesis and medicinal chemistry. 1,2,4-Triazepines, particularly 1,2,4-triazepin-3-ones/ thiones are representatives of these scaffolds [1][2][3][4][5][6]. They are of great interest because of their diverse pharmacological properties.…”

Three-component and one-pot synthesis of 3-aryl-2,4-diselenoxo-1,3,5-triazepane-6,7-diones

“…[3][4][5] Applications of compounds with triazepanedione skeletons have been reported. 6 With regard to monocyclic triazepines, 7 1,2,4-triazepines have been prepared by the cycloaddition of 1-azirines to 1,2,4,5-tetrazines 8 or by a photochemical walk rearrangement of 3,4,7-triaza-2,4-norcaradienes. 9 Although the synthesis of seven-membered [1,2,4]-triazepine derivatives is well precedent in the literature, 10-12 few reports are known for [1,2,5]-triazepine systems.…”