ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19813230416
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