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Hurd–Mori 1,2,3-thiadiazole synthesis

From Wikipedia, the free encyclopedia
Name reaction in organic chemistry
Hurd–Mori 1,2,3-thiadiazole synthesis
Named afterCharles D. Hurd
Raymond I. Mori
Reaction typeRing forming reaction

TheHurd–Mori 1,2,3-thiadiazole synthesis is aname reaction inorganic chemistry that allows for the generation of 1,2,3-thiadiazoles through the reaction ofhydrazone derivatives with anN-acyl orN-tosyl group reacted withthionyl chloride.[1][2][3][4] An analogous reaction gives 1,2,3-selenadiazoles by usingselenium dioxide instead of thionyl chloride.[4]

References

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  1. ^Hurd, Charles D.; Mori, Raymond I. (1995-10-01). "On Acylhydrazones and 1,2,3-Thiadiazoles".Journal of the American Chemical Society.77 (20):5359–5364.doi:10.1021/ja01625a047.
  2. ^Turner, Martin; Linder, Thomas; Schnürch, Michael; Mihovilovic, Marko D.; Stanetty, Peter (2010-07-17). "Investigation of the regioselectivity of the Hurd–Mori reaction for the formation of bicyclic 1,2,3-thiadiazoles".Tetrahedron.66 (29):5472–5478.doi:10.1016/j.tet.2010.05.017.
  3. ^Morzherin, Yuriy Yur`evich; Glukhareva, Tatiana V.; Bakulev, Vasiliy A. (June 2003). "Rearrangements and Transformations of 1,2,3-Thiadiazoles in Organic Synthesis. (Review)".Chemistry of Heterocyclic Compounds.39 (6):679–706.doi:10.1023/A:1025689208261.S2CID 97346885.
  4. ^abThuc, 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.
Carbon-carbon
bond forming
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Homologation reactions
Olefination reactions
Carbon-heteroatom
bond forming
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Degradation
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Organic redox
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Rearrangement
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Ring forming
reactions
Cycloaddition
Heterocycle forming reactions


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