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Regioselective synthesis of substituted triazolium salts via 1,3-dipolar cycloaddition reactions
Faculty
Science
Year:
2003
Type of Publication:
Article
Pages:
1577-1584
Authors:
AMER, AM
DOI:
10.1007/s00706-003-0041-1
Journal:
MONATSHEFTE FUR CHEMIE SPRINGER-VERLAG WIEN
Volume:
134
Research Area:
Chemistry
ISSN
ISI:000187131700010
Keywords :
cycloadditions, olefins, nitriles, triazolium salt, regioselectivity
Abstract:
The regioselectivity of 1,3-dipolar cycloaddition reactions of 1-aza-2-azoniaallene salts with alpha,beta-unsaturated nitriles such as acrylonitrile or cyclohexylidene acetonitrile afforded only 1,2,4-triazolium salts via addition to the nitrile group, while the other expected pyrazolium salts were not observed. Moreover, 1-aza-2-azonia-allene salts reacted with other competitive systems such as alpha-iminonitrile derivatives yielding only triazolium salts via addition to the nitrile and not to the imino group. Treatment of cumulene with 3-pyridylnitrile afforded the pyridinium salt. However, 2,3-dimethyl-5-(2,6-dimethoxyphenyl)-{[}1,2,4]triazole could be prepared from cumulene and 2,6-dimethoxybenzonitrile. Some reactions of nitriles with 1-aza-2-azonia-allene salts prepared from 1,2,3-indantrione and 9-acetylphenanthrene are discussed.
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