1456-21-9Relevant articles and documents
Synthesis of 1,3,4-thiadiazoles from aldehyde hydrazones
Okuma, Kentaro,Nagakura, Kazuko,Nakajima, Yasutaka,Kubo, Kento,Shioji, Kosei
, p. 1929 - 1931 (2004)
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
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.
TiCl4 mediated facile synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
Zhang, Lin,Yu, Yu,Tang, Qiang,Yuan, Jianyong,Ran, Dongzhi,Tian, Binghua,Pan, Tao,Gan, Zongjie
, p. 423 - 431 (2019/12/27)
An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles has been developed. Various hydrazides or thionyl hydrazides readily react with DMA derivatives in the presence of TiCl4 as a catalyst to afford the desired products. This protocol provides a simple and economical procedure that affords the target products with good yields and wide substrate scope.
A KHSO4 promoted tandem synthesis of 1,3,4-thiadiazoles from thiohydrazides and DMF derivatives
Gan, Zongjie,Tian, Binghua,Yuan, Jianyong,Ran, Dongzhi,Zhang, Lin,Dong, Gang,Pan, Tao,Zeng, Yixin,Yu, Yu
supporting information, (2020/07/15)
An efficient, simple and environmentally benign method for the construction of 1,3,4-thiadiazole skeletons via the tandem coupling and cyclization of thiohydrazides with DMF derivatives in the presence of KHSO4 has been reported. This method re
Preparation method of 1, 3, 4-thiadiazole compound and compound prepared by preparation method
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Paragraph 0019-0020; 0061-0062, (2020/12/10)
The invention belongs to the field of medicinal chemistry. Specifically, the invention discloses a preparation method of a 1, 3, 4-thiadiazole compound and the compound prepared by using the preparation method. According to the method, the 1, 3, 4-thiadia
One pot solvent-free solid state synthesis, photophysical properties and crystal structure of substituted azole derivatives
Du, Yanting,Wan, Zilu,Chen, Lianqing,Wu, Lamei
, p. 315 - 325 (2019/05/27)
A solvent-free solid state method has been developed to synthesize three series of substituted azole derivatives (including 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole) in high yields by condensation cyclization of N,N′-bishydrazide derivatives with corresponding cyclization agents, respectively. This general method avoids the use of organic solvents, saves cost and resources, simplifies post-processing and increases reaction rates. These compounds have been fully characterized by 1H NMR, 13C NMR, elemental analysis and MS. The structure of 2,5-di (4-tertbutylphenyl)-1,3,4-oxadiazole has been determined by single crystal X-ray diffraction analysis. The cell parameters are as follows: monoclinic crystal system, Cc space group, a = 18.735 (2) ?, b = 6.3375 (8) ?, c = 16.824 (2) ? and α = γ = 90°; β = 98.292 (2). The electronic absorption and fluorescent properties of these compounds have been systematically investigated for the first time. The relationships between heterocyclic structures and photophysical properties have been discussed. The alteration of emission and absorption wavelengths can be elucidated by hybrid atoms' electronegativity and Substituents' Hammett constants. This approach proposes a novel insight to provide a great number of novel substituted azole derivatives with good photophysical properties by a general green method.
An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent
Ko, Inseok,Park, Soojin,Lee, Goeun,Kim, Hakwon
, p. 67 - 78 (2019/03/07)
Five-membered heterocyclic-ring systems, such as thiadiazoles, remain an important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments, some of the newly synthesized thiadiazoles show antioxidant activity.
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.
Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles
Zhou, Zhen,Liu, Yang,Chen, Jiangfei,Yao, En,Cheng, Jiang
, p. 5268 - 5271 (2016/10/31)
A copper-mediated, three-component reaction between two different N-Ts hydrazones and elemental sulfur was developed, leading to a series of unsymmetric 2,5-disubstituted 1,3,4-thiadiazoles in moderate yields with good functional group compatibility. This
Tetrazine Assists Reduction of Water by Phosphines: Application in the Mitsunobu Reaction
Polezhaev, Alexander V.,Maciulis, Nicholas A.,Chen, Chun-Hsing,Pink, Maren,Lord, Richard L.,Caulton, Kenneth G.
, p. 13985 - 13998 (2016/09/21)
Reaction of 3,6-disubstituted-1,2,4,5-tetrazines with water and PEt3forms the corresponding 1,4-dihydrotetrazine and OPEt3. Thus PEt3, as a stoichiometric reductant, reduces water, and the resulting two reducing equivalent
