- A continuous flow synthesis and derivatization of 1,2,4-thiadiazoles
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A continuous flow process is presented that enables the efficient synthesis and derivatization of 1,2,4-thiadiazole heterocycles. Special attention was given to the safe handling of the versatile yet hazardous trichloromethane sulfenylchloride reagent including its in-line quenching in order to eliminate malodourous and corrosive by-products. Based on this flow method gram quantities of 5-chloro-3-phenyl-1,2,4-thiadiazole were safely prepared allowing for further elaboration of this valuable building block by reaction with different nitrogen-, sulfur- and oxygen-based nucleophiles. This synthetic approach was subsequently applied to generate a series of bromophenyl-5-chloro-1,2,4-thiadiazoles providing a valuable entry towards further structural diversification on this important heterocyclic scaffold.
- Baumann, Marcus,Baxendale, Ian R.
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p. 6218 - 6223
(2017/09/30)
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- A facile synthesis of 3-substituted 5-oxo-1,2,4-thiadiazoles from amidoximes
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The reaction of amidoximes 1 with 1,1′-thiocarbonyldiimidazole (TCDI) followed by treatment with silica gel or boron trifluoride diethyl etherate (BF3·OEt2) provided 3-substituted 4,5-dihydro-5-oxo-1,2,4-thiadiazoles 2 in moderate yi
- Kohara,Kubo,Imamiya,Naka
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p. 1419 - 1423
(2007/10/03)
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- REACTION OF BENZAMIDE OXIME DERIVATIVES WITH CHLOROCARBONYLSULFENYL CHLORIDE
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Benzamide oxime derivatives (1) were reacted with chlorocarbonylsulfenyl chloride (2) in the presence of a base as a catalyst to afford 3-aryl-4,5-dihydro-1,2,4-thiadiazol-5-one (3), 3-aryl-4,5-dihydro-1,2,4-oxadiazol-5-one (4) and di(benzamide) O,O'-carboxime (5) derivatives in moderate yields.The reaction of N-ethyl-p-toluamide oxime (7) with 2 gave 4-ethyl-4,5-dihydro-3-(p-tolyl)-1,2,4-thiadiazol-5-one (8) and 4-ethyl-4,5-dihydro-3-(p-tolyl)-1,2,4-oxadiazol-5-one (9).
- Kawashima, Etsuko,Ando, Yuko,Takada, Toyozo,Tabei, Katsumi
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p. 181 - 190
(2007/10/02)
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