1,2,4-TRIAZINE IN ORGANIC SYNTHESIS. 16. REACTIVITY OF 3-SUBSTITUTED 6-PHENYL-1,2,4-TRIAZINES TOWARDS PHENYLACETONITRILE ANION IN POLAR APROTIC SOLVENTS

Авторы

  • A. Rykowski Institute of Chemistry, University of Podlasie, ul. 3-go Maja 54, 08-110 Siedlce
  • E. Wolińska Institute of Chemistry, University of Podlasie, ul. 3-go Maja 54, 08-110 Siedlce
  • H. C. van der Plas Laboratory of Organic Chemistry, University of Wageningen, Dreijenplein 8, 6703 HB Wageningen

Ключевые слова:

3-substitued 1,2,4-triazines, nucleophilic addition of phenylacetonitrile anion, diastereomeric mixtures of 2,5-dihydrotriazines

Аннотация

The reactions of 3-X-6-phenyl-1,2,4-triazines (X = SMe, SPh, SO2Ph) with phenylacetonitrile anion in DMF were studied. In these reactions the ring transformation product 3-amino-4,6-diphenylpyridazine, the covalent addition product, 3-X-5-(α-cyanobenzyl)-6-phenyl-2,5-dihydro-1,2,4-triazine, and the ipso-substitution product 3-(1-cyano-1-phenylmethyl)-6-phenyl-1,2,4-triazine were obtained. Analogous reactions carried out in DMA gave only the addition products in excellent yields as diastereomeric mixtures of the corresponding 2,5-dihydro-1,2,4-triazines.

How to Cite
Rykowski, A.; Wolińska, E.; van der Plas, H. C. Chem. Heterocycl. Compd. 2001, 37, 1418. [Khim. Geterotsikl. Soedin. 2001, 1549.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1017959403370

Загрузки

Опубликован

2001-11-25

Выпуск

№ 11 (2001)

Раздел

Оригинальные статьи