Cyanoacetylene and its derivatives: XXXIV. Nucleophilic addition of tetrazole to cyanoacetylenes

Nucleophilic addition of tetrazole to 4-hydroxy-4-alkyl-2-aknonitriles 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 degrees C, 13-50 h, 4-15 wt% MOH (M = Na, K), THF (o...

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Published inRussian journal of organic chemistry Vol. 41; no. 8; pp. 1202 - 1207
Main Authors Nosyreva, VV, Mal'kina, AG, Shemyakina, OA, Kositsyna, EI, Albanov, AI, Trofimov, BA
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.08.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
AZOLES
CHEMISTRY
SALTS
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Summary:Nucleophilic addition of tetrazole to 4-hydroxy-4-alkyl-2-aknonitriles 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 degrees 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 degrees C resulted in vinyl nucleophilic substitution of the tetrazole moiety by an ethoxy group.
ISSN:1070-4280
1608-3393
DOI:10.1007/s11178-005-0317-5