Reaction of ethyl acetoacetate with isoquinolinium and pyridinium ylides.

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Reaction of isoquinolinium bis (ethoxycarbonyl) methylide (I) with ethyl acetoacetate gave ethyl 1-acetyl-2-hydroxypyrrolo [2, 1-α] isoquinoline-3-carboxylate (IV), ethyl 2-methylpyrrolo [2, 1-α] isoquinoline-3-carboxylate (V), diethyl 2-methylpyrrolo [2, 1-α] isoquinoline-1, 3-dicarboxylate (VII), and ethyl 2-ethoxycarbonylmethylpyrrolo [2, 1-α]-isoquinoline-3-carboxylate. Similar reaction of isoquinolinium cyano (ethoxycarbonyl)-methylide (II) with ethyl acetoacetate gave 3-cyano-2-methylpyrrolo [2, 1-α] isoquinoline (IX) and ethyl-3-cyano-2-methylpyrrolo [2, 1-α] isoquinoline-1-carboxylate (X) besides compound VIII. Similarly, reaction of pyridinium bis (ethoxycarbonyl) methylide (XI) with ethyl acetoacetate gave ethyl 1-acetyl-2-hydroxyindolizine-3-carboxylate (XIII).

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