Novel 1,5,3-dithiazepanes: three-component synthesis, stereochemistry, and fungicidal activity

Мulticomponent Reactions of NH4Cl, CH2O and SH‐acids in Water as Effective Synthesis of Biologically Active Heterocycles

“…Selective synthesis of bis ‐heterocycle ( 7 ) with yield 67% was realized by mixing 1,2‐ethanedithiol with aqueous solution of formaldehyde (37%) in molar ratio 3:6 and subsequent introducing to the reaction of 2 mol aqueous solution of NH 4 Cl at room temperature (method a , Scheme ). Reducing the temperature to 0°C strongly decreases the fraction of bis ‐heterocycle ( 7 ), whereas the reaction at raised temperature (50–70°C) gives compound ( 7 ) and sulfur‐containing by‐products derived from CH 2 O and 1,2‐ethanedithiol in a total yield of 35%, which was observed earlier . In the mean time, upon mixing of 1,2‐ethanedithiol and CH 2 O (2:2.5) and subsequent introducing of NH 4 Cl and CH 2 O (2:2.5) to the reaction mixture, product ( 7 ) and 3‐(1,5,3‐dithiazepan‐3‐ylmetyl)‐1,5,3‐dithiazepan ( 8 ) were formed at a ratio 1:4 with total yield 42% (method b , Scheme ).…”

Intermolecular interactions and chiral crystallization effects in (1,5,3-dithiazepan-3-yl)-alkanoic acids

“…The co-crystals 2a and 2b were obtained from water and dimethyl sulfoxide solutions of 2-(1,5,3-dithiazepan-3-yl)-acetic acid 2, respectively. 14,16,23,24 The hydroxyl group of compound 1 and the amino acid fragments of 2-4 are in pseudo-axial arrangement relative to the mean plane of the 1,5,3-dithiazepane cycle, whereas the amino acid moieties of 5 and 7 are in a pseudoequatorial position and those of 6 and 8 are in an intermediate arrangement. The same conformation was revealed in the co-crystal 2a and compounds 5-8, whereas dithiazepane cycles in the co-crystal 2b and in molecules 3 and 4 are in pseudo-boat conformation because sulphur atoms deviate from that mean plane by one side.…”

“…[14][15][16][17][18][19][20][21][22] The structure of some compounds was unequivocally determined with the use of an X-ray tech-nique. [14][15][16][17][18][19][20][21][22] The structure of some compounds was unequivocally determined with the use of an X-ray tech-nique.…”

The synthesis of N-substituted N,S-macroheterocycles derived from aromatic carboxylic acid hydrazides

“…There are stereoelectronic interactions between the unshared electrons on the nitrogen and sulfur atoms (for instance, in the dithiazinane [17,18] and dithiazepinane [19] systems), that reduce the energy of the chair conformation and the chair-chair conformation, respectively. However, the macrocycle has a higher conformational mobility, so the number of possible conformations increases.…”