The 1,2,3-dithiazole is an underappreciated scaffold in medicinal chemistry despite possessing a wide variety of nascent pharmacological activities. The scaffold has a potential wealth of opportunities within these activities and further afield. The...
The crystal structure and solid-state packing of 4-chloro-5H-1,2,3-dithiazol-5-one and two polymorphs of 4-chloro-5H-1,2,3-dithiazole-5-thione were analyzed and compared to structural data of similar systems. These five-membered S,N-rich heterocycles...
A new general protocol for synthesis of fused 1,2,3-dithiazoles by the reaction of cyclic oximes with S2Cl2 and pyridine in acetonitrile has been developed. The target 1,2,3-dithiazoles fused with various carbocycles, such as indene, naphthalenone, c...
The reactions of 2-, 3- and 4-aminopyridines with 4,5-dichloro-1,2,3-dithiazol-ium chloride (Appel salt) 4 to give N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)pyridin-X-amines 1a (X = 2), 1g (X = 3) and 1k (X = 4) were optimized with respect to base, te...
Background/Objectives: Biofilm-associated infections pose a major clinical challenge since bacteria within biofilms exhibit highly antibiotic tolerance. Pseudomonas aeruginosa forms persistent biofilms that cause chronic infections in vulnerable pati...
We report our investigations into the underlying differences between 1,2,3-dithiazole and their ultra-rare counterpart, 1,2,3-thiaselenazole. This rare 1,2,3-thiaselenazole chemotype was afforded by sulfur extrusion and selenium insertion into the pr...
Alkylidene oxindoles are important functional moieties and building blocks in pharmaceutical and synthetic chemistry. Our interest in biologically active compounds focused our studies on the synthesis of novel oxindoles, bearing on the exocyclic doub...
Reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-[amino(methylthio)methylene])malononitrile (1 equiv) in the presence of pyridine (2 equiv) gave (Z)-2-{[(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile in 20...
A new synthetic pathway to four substituted imidazoles from readily available 2-((4-aryl(thienyl)-5H-1,2,3-dithiazol-5-ylidene)amino)phenols has been developed. Benzo[d]oxazol-2-yl(aryl(thienyl))methanimines were proved as key intermediates in their...
The structure–property correlations and control of electronic excited states in transition metal complexes (TMCs) are of high significance for TMC-based functional material development. Within these studies, a series of Re(I) carbonyl complexes...
The high yielding transformations of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (up to 85%) and 2-(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (up to 83%) have been investigated and compared to t...
The benzo[1,2,3]dithiazole is a unique heteroaromatic functionality whose conjugated profile instils some fascinating electronic properties. This has been historically recognized in the design and manufacture of organic dyes early last century. Altho...
(Z)-2-(4-Chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile 1, when treated with either triphenylphosphine (4 equiv.) or polymer bound triphenylphosphine (5 equiv.) in dichloromethane at room temperature for 3 days...
The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-(phenylsulfonyl)acetonitrile (1 equiv) in the presence of pyridine (2 equiv) gave S-(3-chloro-5-cyanoisothiazol-4-yl)benzenesulfonothioate and (Z)-2-(4-chloro-5H-1,2,3-dithiazol-5-yliden...
Thermolysis of 4,4′-dichloro-, 4,4′-diaryl-, and 4,4′-di(thien-2-yl)-5,5′-bi(1,2,3-dithiazol-ylidenes) affords the respective 3,6-dichloro-, 3,6-diaryl- and 3,6-di(thien-2-yl)isothiazolo[5,4-d]-isothiazoles in low to high yiel...
2-Amino-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile 1 reacts with 4,5-dichloro-1,2,3-dithiazolium chloride 2 in the presence of pyridine (2 equiv.) to afford (Z)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5- dicarboni...
This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adduc...
We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieve...
A series of monosubstituted acetonitriles were treated with disulfur dichloride atroom temperature in CH2Cl2 to afford 5-substituted-4-chloro-1,2,3-dithiazolium chlorides 1.Where the 5-substituent was not a good leaving group the chloride salts were...
N-Aryl-S,S-dimethylsulfimides 3(Ar = 4-NO2C6H4), 4 (Ar = Ph) and 5 (Ar = 4-Tol)react with Appel salt 1 to give the corresponding N-aryl-(4-chloro-5H-1,2,3-dithiazolylidene)benzenamines 8 (Ar = 4-NO2C6H4), 9 (Ar = Ph) and 10 (Ar = 4-Tol) in 84, 94 and...
Based on the extensive biological activities of thiazole derivatives against different types of diseases, we are interested in the effective part of many natural compounds, so we synthesized a new series of compounds containing di-, tri- and tetrathi...
Active methylene compounds such as thioamides are widely used in the organic chemistry for the construction of a variety of heterocyclic systems, such as thieno[2,3-b]pyridines, 1,2,4-dithiazoles, isothiazoles, 1,2,3-thiadiazoles, etc. N,N′-Dip...
High-performance organic semiconductors should have good spectral absorption, a narrow energy gap, excellent thermal stability and good blend film morphology to obtain high-performance organic photovoltaics (OPVs). Therefore, we synthesized two IDTz-...