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SYNTHETIC TRANSFORMATIONS OF ISOQUINOLINE ALKALOIDS: 1-(N-ALKYL-1,2,3-TRIAZOL-4-YL)-6,18-endo-ETHENODIHYDROTHEBAINEHYDROQUINONES AND TRIAZOLYLNAPHTHOHYDROQUINONE-CONTAINING BENZOFUROAZOCINES FROM THEBAINE

Валентина Т. Бауман, Жамсранжав Ганбаатар, Эльвира Э. Шульц
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Abstract


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.

Authors: Valentina T. Bauman, Jamsranjav Ganbaatar, Elvira E. Shults*


Keywords


benzofuroazocines; dihydrothebainehydroquinone; thebaine; 1,2,3-triazoles; Cu(I)-catalyzed reactions; retro-cleavage

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