Thiadiazoles

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}} }}

In chemistry, '''thiadiazoles''' are a sub-family of azole compounds, with the name ''thiadiazole'' originating from the Hantzsch–Widman nomenclature. Structurally, they are five-membered heterocyclic compounds containing one sulfur and two nitrogen atoms. The ring is aromatic by virtue of the two double bonds and one of the lone pairs of electrons of sulfur. Four constitutional isomers are possible, differing by the relative positions of the sulfur and nitrogen atoms. The nomenclature thus includes the locations of each of those three atoms, with the first of the three numbers referring to the sulfur.

The parent compounds are rarely synthesized and possess no particular application, however, compounds bearing them as a structural motif are fairly common in pharmacology. Of them, 1,3,4-thiadiazole is the most common, appearing in such medications as cephazolin and acetazolamide.<ref name="HuLi2014">{{cite journal|last1=Hu|first1=Yang|last2=Li|first2=Cui-Yun|last3=Wang|first3=Xiao-Ming|last4=Yang|first4=Yong-Hua|last5=Zhu|first5=Hai-Liang|title=1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry|journal=Chemical Reviews|volume=114|issue=10|year=2014|pages=5572–5610|issn=0009-2665|doi=10.1021/cr400131u|pmid=24716666}}</ref><ref name="JainSharma2013">{{cite journal|last1=Jain|first1=Abhishek Kumar|last2=Sharma|first2=Simant|last3=Vaidya|first3=Ankur|last4=Ravichandran|first4=Veerasamy|last5=Agrawal|first5=Ram Kishore|title=1,3,4-Thiadiazole and its Derivatives: A Review on Recent Progress in Biological Activities|journal=Chemical Biology & Drug Design|volume=81|issue=5|year=2013|pages=557–576|issn=1747-0277|doi=10.1111/cbdd.12125|pmid=23452185|doi-access=free}}</ref><ref name="DehaenBakulev2004">{{cite book|author1=Wim Dehaen|author2=Vasiliy A. Bakulev|author3=Edward C. Taylor|author4=Jonathan A. Ellman|title=The Chemistry of Heterocyclic Compounds, The Chemistry of 1,2,3-Thiadiazoles|url=https://books.google.com/books?id=-XMt2cdjIfAC&pg=PR5|date=27 April 2004|publisher=John Wiley & Sons|isbn=978-0-471-65691-3|pages=5–}}</ref>

3,4-Dichloro-1,2,5-thiadiazole arises readily from cyanogen.

In the Hurd–Mori reaction, an acyl hydrazone reacts with thionyl chloride to give a 1,2,3-thiadiazole.<ref name=Thuc>{{cite journal |last1=Thuc |first1=Dinh Ngoc |title=Synthesis and characterization of some new 1,2,3-thiadiazole and 1,2,3-selenadiazole triterpene derivatives from allobetulone and 2-oxoallobetulin |journal=Synthetic Communications |date=2020 |volume=50 |issue=11 |pages=1665–1671 |doi=10.1080/00397911.2020.1750655|s2cid=219092397 }}</ref>

==References== {{Reflist}}

Category:Thiadiazoles Category:Functional groups