1,3,4-Thiadiazoles

Koutentis, P. A.; Constantinides, Christos P.

doi:10.1016/b978-008044992-0.00510-1

Cited by 14 publications

(8 citation statements)

References 204 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is known that 1,3,4-oxadiazoles [ 26 ], 1,3,4-thiadiazole [ 27 ] and 1,2,4-triazoles [ 28 – 30 ] can be obtained from diacylhydrazines. Thus, 11 and 12 were converted to 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazole ( 13 ) and 2,5-bis[4-(hexyloxy)-2,2'-bithiophen-5-yl]-1,3,4-oxadiazole ( 14 ) by the reaction with phosphorus oxychloride, in 78 and 83% yields, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

Kostyuchenko¹,

Yurpalov²,

Kurowska³

et al. 2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryA new synthetic approach towards the preparation of functionalised, soluble, donor–acceptor (DA) alkylbithiophene derivatives of oxadiazole, thiadiazole and triazole is reported. Taking advantage of the Fiesselmann reaction, reactive bithiophene synthons having alkyl or alkoxy substituents at designated positions are prepared. Following a synthetic strategy, featuring the bottom-up approach, sequential structural elements are built, starting from a simple thiophene compound, until the target molecule is obtained, all in good yield. Supplementing the well established methods of oxadiazole and thiadiazole synthesis, efficient ring closure reaction affording a 4H-1,2,4-triazole unit is presented. All target ambipolar compounds display strong photoluminescence with measured quantum yields up to 0.59. Modification of the demonstrated synthetic routes may be exploited for the preparation of longer, specifically functionalised oligothiophenes, coupled to other heteroaromatic cores.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

Kostyuchenko¹,

Yurpalov²,

Kurowska³

et al. 2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Thiadiazoles are five-membered heterocyclic arrangements which are rarely found in nature. Nitrogen, sulfur and carbon atoms can be arranged in several different ways in such a ring, which gives rise to several isomers: 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole and 1,3,4-thiadiazole [ 1 , 2 ]. Of these four isomers, derivatives of 1,3,4-thiadiazole seem to be the most popular among scientists.…”

Section: Introductionmentioning

confidence: 99%

1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure

et al. 2020

View full text Add to dashboard Cite

Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, N,N-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by 1H-NMR, 13C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.

show abstract

“…Thus, it has been reported that 1,3,4-thiadiazolidine-2,5-dithione 803 with dialkylamines and formaldehyde give N,S-aminomethylated thiadiazoles 804. With urea, thiourea, semicarbazide, or thiosemicarbazide N,Naminomethylated thiadiazoles 805 have been obtained (Scheme 14.230) [258].…”

Section: Reactivitymentioning

confidence: 99%

“…In particular, 1,3,4-thiadiazoles are used in medicine, as antimicrobial [248], antituberculosis [249], anti-inflammatory [250], anticonvulsant [251], antihypertensive [252], local anesthetic [253], anticancer [254], and hypoglycaemic compounds [255]. This ring system has been the subject of several reviews [256][257][258]; this chapter will be essentially devoted to the recent published reports (2000-2008).…”

mentioning

confidence: 98%