The title compound, C17H18N2S2, exhibits a trans-trans-trans-gauche(+) (tttg (+)) conformation with regard to the NH-CH2-CH2-CH2-NH bond sequence. In the crystal, mol-ecules are connected by N-H⋯S=C and C-H⋯S=C hydrogen bonds, forming a herringbone arrangement along the c-axis direction. The two thioamide groups make dihedral angles of 43.0 (2) and 33.1 (2)° with the adjacent phenyl rings.

The molecular frame of the reported series of new polyheterocyclic compounds was intended to combine the potent phenothiazine and benzothiazole pharmacophoric units. The synthetic strategy applied was based on oxidative cyclization of N-(phenothiazin-3-yl)-thioamides and it was validated by the preparation of new 2-alkyl- and 2-aryl-thiazolo[5,4-b]phenothiazine derivatives. Optical properties o...

The title salt, C6H7N2S(+)·I(-), crystallizes with two independent cations and two anions in the asymmetric unit. In one of the cations, the dihedral angle between the pyridinium ring and the thioamide group is 28.9 (2)°; in the other it is 33.5 (2)°. In the crystal, N-H⋯S and C-H⋯S hydrogen bonds link the independent cations into pairs. These pairs form a three-dimensional network through addi...

The Ag(I)-promoted coupling of amino acids and peptides with amino ester thioamides generates peptide imides without epimerisation. The peptide imides undergo regioselective hydrolysis under mild conditions to generate native peptides. This method was employed to prepare the pentapeptide thymopentin in the N→C direction, in high yield and purity.

Metal-free, p-toluenesulfonic acid (p-TSA)-mediated, straightforward propargylation of β-ketothioamides with aryl propargyl alcohol has been achieved at room temperature. In addition, the reaction also provided thiazole rings as byproducts. Furthermore, the propargylated thioamides undergo intramolecular 1,5-cyclization to afford fully substituted (hydro)thiophenes in the presence of base. Nota...

The synthesis of a bridged thiolactam is described. This thiolactam is shown to undergo an unusual C-N bond cleavage reaction under conditions of its synthesis. Spectroscopic properties of the thiolactam indicate a considerable degree of twist of the thioamide bond.

Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partak...