- One-pot synthesis of 1,3,4-oxadiazol-2(3H)-ones with CO2 as a C1 synthon promoted by hypoiodite
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A convenient and efficient route has been developed to synthesize 1,3,4-oxadiazol-2(3H)-ones from CO2, hydrazines and aryl or aliphatic aldehydes. Promoted by hypoiodite (IO-) generated in situ from KI and oxidant TBHP, the one-pot synthesis could proceed smoothly to afford the desired products in moderate to high yields. Mechanism studies revealed that nitrile imine was an important intermediate in this transformation. Notably, a commercial herbicide Oxadiazon could be successfully synthesized by this route.
- Yang, Na,Yuan, Gaoqing
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p. 6639 - 6644
(2019/07/16)
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- The reaction of sydnones with bromine in acetic anhydride revisited: A new route to 5-substituted-3-aryl-1,3,4-oxadiazol-2(3H)-ones from N-aryl-N-bromocarbonylhydrazines
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The reaction of 3-phenylsydnone with bromine in acetic anhydride to form 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one has been reexamined and improved. A new mechanism involving a bromocarbonylhydrazine species is proposed and its intermediacy is supported
- Tumey, Jonathan M.,Gerritsen, Thijs,Klaasen, Jimmy,Madaram, Karunakar R.,Turnbull, Kenneth
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