Abstract
Reactions of Malonanilic Acid Ethyl Esters with HeterocumulenesMalonanilic acid ethyl esters 1 react with carbon disulfide in the presence of sodium hydride to give disodium salts 2. Treatment of 2 with an alkylation reagent yields the openchain or cyclic ketene S,S‐acetals 3 and 4, respectively. Adding only one equivalent of methyl iodide to 2 and acidifying the reaction mixture lead to the dithioesters 5. Reaction of 3 with amines or o‐amino‐thiophenol yields S,N‐ and N,N‐acetals only in some cases. S,N‐acetals 6 are further available by addition of phenyl isothiocyanate to 1 whereas N,N‐acetals are synthesized, too, by chlorination of 3 and reaction with amines. Acidifying of 11 gives the thioacetoanilides 12. Some more reactions (oxidation of 3a, d and saponification/decarboxylation of 4a) are discussed.
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