Nitrosation of methyl 2-acylamino-3-dimethylaminopropenoates. A simple conversion of n-acylglycines into 5-substituted 1,2,4-Oxadiazole-3-carboxylates |
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Authors: | Matej Kmeti Branko Stanovnik |
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Institution: | Matej Kmetiĉ,Branko Stanovnik |
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Abstract: | A novel simple synthesis of 5-substituted-1,2,4-oxadiazole-3-carboxylates 5 from N-acylglycines 1 , which are transformed with DMF in the presence of phosphorus oxychloride into 2-substituted-4-dimethyl-aminomethyleneoxazol-5(4H)-ones 2 , followed by opening into 2-aroylamino-3-dimethylamino-propenoates 3 , and nitrosation to give the oximes 4 as intermediates, which cyclize spontaneously into 5-substituted-1,2,4-oxadiazole-3-carboxylates 5 . The compounds 2 can be transformed into 5 without isolation of 3 and 4 . |
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