1,3-Oxazines and Related Compounds. V. N-Acylacetylation of Carboxamides with the Diketene-Halotrimethylsilane System or Acyl Meldrum's Acids
Various aliphatic and aromatic carboxamides smoothly underwent N-acetoacetylation by means of the diketene-iodotrimethylsilane system to give the corresponding N-acetoacetyl derivatives.The diketene-bromotrimethylsilane system was found to be very efficient for N-acetoacetylation of unsaturated carboxamides such as acrylamide and methacrylamide.In addition, acyl Meldrum's acids proved effective for N-acylacetylation of carboxamides, especially heterocyclic carboxamides such as picolinamides.Keywords: carboxamide; acylacetylation; diketene; iodotrimethylsilane; bromotrimethylsilane; acyl Meldrum's acid
Yamamoto, Yutaka,Ohnishi, Shuhei,Azuma, Yutaka
p. 3505 - 3512
(2007/10/02)
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