Cyanoacetylene and Its Derivatives: XXXIV. Nucleophilic Addition of Tetrazole to Cyanoacetylenes

Nucleophilic addition of tetrazole to 4-hydroxy-4-alkyl-2-alkynonitriles and to 3-phenyl-2-propynonitrile occurred regiospecifically and afforded E-, Z-4-hydroxy-4-methyl-3-tetrazolyl-2-alkenonitriles and 3-tetrazolyl-3-phenyl-2-propenonitrile [20–40°C, 13–50 h, 4–15 wt% MOH (M = Na, K), THF (or DMSO)] in up to 69% yield. The attempt to perform cyclization of the hydroxy-containing adducts into iminodihydrofurans (KOH, ethanol, 23-25°C) resulted in vinyl nucleophilic substitution of the tetrazole moiety by an ethoxy group.