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Thiadiazoles

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Thiadiazoles
1,2,3-Thiadiazole
1,2,4-Thiadiazole
1,2,5-Thiadiazole
1,3,4-Thiadiazole
Identifiers
ChEBI
EC Number
  • 1,3,4: 869-482-5
UNII
  • 1,2,3: InChI=1S/C2H2N2S/c1-2-5-4-3-1/h1-2H
    Key: UGUHFDPGDQDVGX-UHFFFAOYSA-N
  • 1,2,4: InChI=1S/C2H2N2S/c1-3-2-5-4-1/h1-2H
    Key: YGTAZGSLCXNBQL-UHFFFAOYSA-N
  • 1,2,5: InChI=1S/C2H2N2S/c1-2-4-5-3-1/h1-2H
    Key: UDGKZGLPXCRRAM-UHFFFAOYSA-N
  • 1,3,4: InChI=1S/C2H2N2S/c1-3-4-2-5-1/h1-2H
    Key: MBIZXFATKUQOOA-UHFFFAOYSA-N
  • 1,2,3: C1=CSN=N1
  • 1,2,4: C1=NSC=N1
  • 1,2,5: C1=NSN=C1
  • 1,3,4: C1=NN=CS1
Properties
Molar mass 86.11 g·mol−1
Related compounds
Related compounds
Thiadiazine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

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.[1] [2] [3]

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.[4]

References

[edit ]
  1. ^ Hu, Yang; Li, Cui-Yun; Wang, Xiao-Ming; Yang, Yong-Hua; Zhu, Hai-Liang (2014). "1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry". Chemical Reviews. 114 (10): 5572–5610. doi:10.1021/cr400131u. ISSN 0009-2665. PMID 24716666.
  2. ^ Jain, Abhishek Kumar; Sharma, Simant; Vaidya, Ankur; Ravichandran, Veerasamy; Agrawal, Ram Kishore (2013). "1,3,4-Thiadiazole and its Derivatives: A Review on Recent Progress in Biological Activities". Chemical Biology & Drug Design. 81 (5): 557–576. doi:10.1111/cbdd.12125 . ISSN 1747-0277. PMID 23452185.
  3. ^ Wim Dehaen; Vasiliy A. Bakulev; Edward C. Taylor; Jonathan A. Ellman (27 April 2004). The Chemistry of Heterocyclic Compounds, The Chemistry of 1,2,3-Thiadiazoles. John Wiley & Sons. pp. 5–. ISBN 978-0-471-65691-3.
  4. ^ Thuc, Dinh Ngoc (2020). "Synthesis and characterization of some new 1,2,3-thiadiazole and 1,2,3-selenadiazole triterpene derivatives from allobetulone and 2-oxoallobetulin". Synthetic Communications. 50 (11): 1665–1671. doi:10.1080/00397911.2020.1750655. S2CID 219092397.

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