Abstract
The 1: 1 zwitterionic intermediates obtained from the reaction between N-methylimidazole with dialkyl acetylenedicarboxylates have been trapped by aroyl cyanides to produce highly functionalised 7-aryl-7-cyano-1-methyl-1,8a-dihydro-7H-imidazo[2,1-b] [1,3]oxazines in good yield.
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