Abstract
The reaction of cyclic CH-acids such as 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, 4-hydroxy-6-methyl-2H-pyran-2-one, or 4-hydroxycumarin with dialkyl acetylene dicarboxylates in the presence of tosylmethyl isocyanide (TosMIC) in polyethylene glycol (PEG-300) leads to new annulated highly functionalised 2-amino-4H-pyrans at room temperature in good yields.
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