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An efficient synthetic method was developed to access isoquinoline-derived diene esters from enynones and isoquinoline- N -oxides in an atom-economic manner. The isoquinoline-substituted diene esters were obtained in moderate to excellent yields via [3 + 2]-cycloaddition and isoxazole ring opening followed by a [1,5]-sigmatropic rearrangement reaction, which resulted in one C-C and two C-O bond formations. Further, quinolin-2(1 H )-ylidene-substituted 1,5-diones were achieved by reaction of enynones with quinoline- N -oxides in very good to high yields.

Gold(I)-catalyzed efficient synthetic transformation was achieved to access the tetrahydrobenzo[ h ]cyclopropa[ c ]chromenes from allyl-substituted 1,6-diynes. Cyclopropane-fused tetrahydrobenzochromenes were obtained regioselectively in ≤92% yields. In this atom-economic organic transformation, three new C-C bonds were formed sequentially in one pot.

An efficient synthetic organic transformation was developed to access isoquinoline-substituted isobenzofurans by reaction of substituted 1,5-diynes with isoquinoline N -oxides. Moderate to excellent yields of isoquinoline-derived isobenzofurans were achieved by formation of a new C-C and two C-O bonds in the presence of copper catalyst in one pot. whereas quinoline-substituted isobenzofurans were obtained when the reaction was conducted using quinoline N -oxides and 1,5-diynes in the presence copper catalyst.