17452-97-0Relevant academic research and scientific papers
Structural studies of 2,5-disubstituted 1,3,4-thiadiazole derivatives from dithioesters under the mild condition: Studies on antioxidant, antimicrobial activities, and molecular docking
Gowda, Kemparaje,Kanchugarkoppal, Rangappa S.,Kempegowda, Mantelingu,Nagarakere, Sandhya C.,Rangappa, Shobith,Swarup, Hassan A.
, (2020/04/27)
A series of 2,5-disubstituted 1,3,4-thiadiazole was synthesized and evaluated for their antioxidant and molecular docking studies. These molecules were efficiently synthesized under mild and inexpensive starting material. Construction of these molecules developed using substituted aldehydes and substituted dithioesters in presence of NCS (N-Chorosuccinimide). The compounds 4a, 4b, 4c, 4f, and 4k showed good antibacterial and antioxidant activity among which, 4k possess excellent antibacterial and antioxidant activity. The results of antioxidant activity studies revealed that compound 4k manifested profound antioxidant potential. The molecular docking study was performed with respective newly synthesized compounds to ascertain the binding mode of 4k with respect to the critical proteins involved in biosynthesis and metabolic pathways.
One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent
Zarei, Maaroof
, p. 1867 - 1872 (2017/03/11)
A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology for 1,3,4-thiadiazole synthesis has the advantage of simplicity, ambient reaction conditions, easy purification and good to excellent yield of products.
Solvent-Free Green Synthesis of Azines and Their Conversion to 2,5-Disubstituted-1,3,4-thiadiazoles
Shridevi, D. Doddramappa,Ningaiah, Srikantamurthy,Kuduva, Narayan U.,Yhya, Raad K.,Rai, Kuriya M. Lokanatha
supporting information, p. 2869 - 2875 (2015/12/23)
A solvent-free, clean, and efficient method has been developed for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via azines. This approach exploits the synthetic potential of clean reactions and offers many advantages such as excellent product yie
Rapid synthesis of 2,5-disubtituted 1,3,4-thiadiazoles under microwave irradiation
Lebrini, Mounim,Bentiss, Fouad,Lagrenee, Michel
, p. 991 - 994 (2007/10/03)
The one pot, three-components condensation of aromatic aldehydes, hydrazine and sulfur in ethanol under microwave irradiation provided symmetrically 3,5-disubstituted 1,3,4-thiadiazoles in high yields and good purity. This reaction must be conducted under pressure of hydrogen sulfide produced in-situ. The structure of the compounds was confirmed by 1H, 13C NMR, MS and elemental analysis.
Synthesis of 1,3,4-thiadiazoles from aldehyde hydrazones
Okuma, Kentaro,Nagakura, Kazuko,Nakajima, Yasutaka,Kubo, Kento,Shioji, Kosei
, p. 1929 - 1931 (2007/10/03)
Reaction of p-tolualdehyde hydrazone with disulfur dichloride in the presence of DBU gave 2,5-di (p-tolyl)-1,3,4-thiadiazole (1a) in 54% yield. Phenyldiazomethane also reacted with disulfur dichloride to afford 2,5-diphenyl-1,3,4-thiadiazole (1b) in 80% y
The Oxidation of 1-Thioaroylsemicarbazides
Kurzer, Frederick,Doyle, Kevin M.
, p. 1873 - 1880 (2007/10/02)
Oxidation of 1-thioaroylsemicarbazides by bromine or hydrogen peroxide yields bis(C-aryl-N-ureido)formimidoyl disulphides.As a novel class of the generally labile di-imidoyl disulphides, such products display unusual stability; however, upon acylation, me
A New Synthesis of Symmetrical 2,5-Diaryl-1,3,4-thiadiazoles
Mazzone, Gioacchino,Puglisi, Giovanni,Bonina, Francesco,Corsaro, Antonino
, p. 1399 - 1401 (2007/10/02)
Treatment of aromatic aldehydes with sulfur and hydrazine hydrate in the ratio 1:2:3, respectively, under the Willgerodt conditions affords the title compounds in excellent yields and in a good state of purity.Under the same conditions 2-chloro and 2,6-dichlorobenzaldehyde yield 3H-1,2-benzodithiole-3-thione and bis(2,6-dichlorobenzyl)tetrasulfide, respectively.
Synthesis of Annelated 1,3,4,6-Thiatriazepines from Reaction of Cyclic Thioureas with 1,4-Dichloro-2,3-diazabutadienes
Moss, Stephen F.,Taylor, David R.
, p. 1999 - 2006 (2007/10/02)
Acyclic thioureas react with 1,4-dichloro-1,4-diphenyl-2,3-diazabutadiene in the presence of triethylamine or sodium hydride to give mainly 2,5-diphenyl-1,3,4-thiadiazole.By contrast, the cyclic thioureas imidazoline-2-thione, dihydropyrimidine-2-thione, 4-oxopyrimidine-2-thione, 6-methyl-4-oxopyrimidine-2-thione, and benzimidazole-2-thiol, react with 1,4-dichloro-1,4-diphenyl-2,3-diazabutadiene, and, in the case of imidazoline-2-thione, also with 1,4-dichloro-1,4-bis(4-chlorophenyl)-2,3-diazabutadiene, in the presence of a two-molar proportion of sodium hydride, to give the series of 2,5-diphenyl--1,3,4,6-thiatriazepines: (7a) (35percent), (7b) (63percent), (9a) (36percent), (9b) (26percent), (98) (49percent), and (7c) (29percent), respectively.Formation of the thiatriazaepines is accompanied by variable amounts of 2,5-diaryl-1,3,4-thiadiazoles (2a,b).Acid hydrolysis of the diarylthiatriazepines yields a mixture of breakdown products, of which the principal components are the diphenylthiadiazole (2a) (12-90percent), 2,5-diphenyl-1,3,4-oxadiazole , the corresponding thione (21-22percent), and, from the thiatriazepinones (9a and b), the corresponding pyrimidinediones (15a and b) (81-95percent).The thiatriazepine (7a) reacts with sodium ethoxide to give a ring-opened product, believed to be 1-ethoxy-4-(2-thioxoimidazolin-1-yl)-1,4-diphenyl-2,3-diazabutadiene (18) (77percent).
