Synthesis of new 5-aza-isosteres of guanine containing aryl and hetaryl substituents on the 1,2,4-triazole ring

[Display omitted] The oxidative cyclization of 4-amino-substituted 6-arylidene(hetarylmethylidene)hydrazinyl-1,3,5-triazin-2-ones with lead(IV) tetraacetate proceeds via a Dimroth-type rearrangement to give 5-amino-substituted 2-aryl(hetaryl)-1,2,4-triazolo[1,5-a]-1,3,5-triazin-7-ones. IR, NMR, and...

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Bibliographic Details
Published in:Tetrahedron letters 2015-02, Vol.56 (9), p.1103-1106
Main Authors: Zavodskaya, Anna V., Bakharev, Vladimir V., Parfenov, Victor E., Gidaspov, Alexander A., Slepukhin, Pavel A., Isenov, Maksim L., Eltsov, Oleg S.
Format: Article
Language:English
Subjects:
Cyclization
Fused-ring systems
Nitrogen heterocycles
Rearrangement
Tautomerism
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Summary:[Display omitted] The oxidative cyclization of 4-amino-substituted 6-arylidene(hetarylmethylidene)hydrazinyl-1,3,5-triazin-2-ones with lead(IV) tetraacetate proceeds via a Dimroth-type rearrangement to give 5-amino-substituted 2-aryl(hetaryl)-1,2,4-triazolo[1,5-a]-1,3,5-triazin-7-ones. IR, NMR, and X-ray studies have shown that the only products of the reactions were the [1,5-a]-isomers.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.01.151