Synthesis and cyclization of 1-arylalk-1-ene-3,5-diynylamines |
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Authors: | V N Sorokoumov S N Morozkina I A Balova |
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Institution: | (1) Chemical Faculty, Saint Petersburg State University, Saint Petersburg, 198504, Russia |
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Abstract: | An investigation of the reaction of 1-lithio-1,3-diynes, generated in situ, with nitriles has been carried out. In the case
of aromatic nitriles 1-arylalk-1-ene-3,5-diynylamines are formed, which undergo dimerization and cyclization on isolation,
giving 3-(alka-1,3-diynyl)-4-(alk-2-ynyl)-2,6-diarylpyridines. The effect of the nature of the substituent in the benzonitrile
molecule on the selectivity of the reaction and the yield of the products has been determined. A scheme is proposed for the
conversions and the structures of the intermediates have been established.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 701–710, May, 2006. |
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Keywords: | 3-(alka-1 3-diynyl)-4-(alk-2-ynyl)-2 6-diarylpyridines lithium 2-aminoethylamide 1-arylalk-1-en-3 5-diynylamines diacetylenes 1-lithio-1 3-diynes nitriles prototropic isomerization |
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