SYNTHESIS AND CYCLIZATION OF 1-ARYLALK-1-ENE-3,5-DIYNYLAMINES

Authors

  • В. Н. Сорокоумов Chemical Faculty, Saint Petersburg State University, Saint Petersburg 198504
  • С. Н. Морозкина Chemical Faculty, Saint Petersburg State University, Saint Petersburg 198504
  • И. А. Балова Chemical Faculty, Saint Petersburg State University, Saint Petersburg 198504

DOI:

https://doi.org/10.1007/7975

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

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.

How to Cite
Sorokoumov, V. N.; Morozkina, S. N.; Balova, I. A.  Chem. Heterocycl. Compd. 2006, 42, 615. [Khim. Geterotsikl. Soedin. 2006, 701.]

For this article in the English edition, see DOI 10.1007/s10593-006-0136-9


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Published

2023-08-17

Issue

No. 5 (2006)

Section

Original Papers