Synthetic transformations of isoquinoline alkaloids: 1-( N-alkyl-1,2,3-triazol-4-yl)-6,18- endo-ethenodihydrothebainehydroquinones and triazolylnaphthohydroquinone-containing benzofuroazocines from thebaine.

1-Ethynyl-6,18- endo-ethenodihydrothebainehydroquinone reacted with azides in the presence of CuSO4·5H2O and sodium ascorbate in DMF, forming the respective 1-( N-alkyl(arylalkyl)triazol-4-yl)-6,18- endo-ethenodihydrothebainehydroquinones, which underwent retrodiene cleavage upon heating in DMF, forming functionalized tetrahydrofuro[4,3,2- fg][3]benzazocines containing naphthohydroquinone and 1,2,3-triazolyl substituents. [ABSTRACT FROM AUTHOR]