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SYNTHESIS AND TRANSFORMATIONS OF 4-PHENYLETHYNYLAND 4-STYRYLPYRAZOLO[5,1-c][1,2,4]TRIAZINES

Сергей М. Иванов, Денис С. Колтун
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Abstract


Rearrangements of 3-tert-butyl-8-methyl-4-phenylethynyl-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine derivatives by the action of bases led to the formation of aromatic (E)- or (Z)-4-styryl-functionalized compounds. At the same time, 4-styryl-1,4-dihydropyrazolotriazines did not rearrange to form the expected 4-phenylethylpyrazolo[5,1-c][1,2,4]triazine. The latter was obtained via an alternative route by the addition reaction of phenylethynylmagnesium bromide to 3-tert-butyl-8-methylpyrazolo[5,1-c][1,2,4]triazine, as well as by reduction of double bonds in the ring and side chain of the 4-styryl derivative with subsequent selective oxidation by N-bromosuccinimide. The spectral and X-ray structural data as well as the antimicrobial properties of the synthesized compounds are discussed.

Keywords


1,2,4-triazine; bromination; hydride shift; oxidation; rearrangement; reduction.

Full Text: PDF (Russian) Supplementary File(s): Supplementary information (105MB)


 

 

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