Synthesis of new 5-aza-isosteres of guanine - 5-aminosubstituted 1,2,4-triazolo[1,5-a]-1,3,5-triazin-7-ones / Bakharev V.V., Parfenov V.E., Ul'Yankina I.V., Zavodskaya A.V., Selezneva E.V., Gidaspov A.A., Eltsov O.S., Slepukhin P.A. // Tetrahedron. - 2014. - V. , l. 38. - P. 6825-6830.

ISSN:
00404020
Type:
Article
Abstract:
The reaction of 4-amino-substituted 6-hydrazinyl-1,3,5-triazin-2(1H)-ones with orthoformate proceeds via the Dimroth-type rearrangement to give 5-amino-substituted 1,2,4-triazolo[1,5-a]-1,3,5-triazine-7-ones. IR, NMR and X-ray studies have shown that the only product of the reaction was the [1,5-a]-isomer as prototropic 3H- and 6H-tautomers. © 2014 Elsevier B.V. All rights reserved.
Author keywords:
Nitrogen heterocycles Cyclization Fused-ring systems Tautomerism Rearrangement
Index keywords:
1,2,4 triazolo[1,5 a] 1,3,5 triazin 7 one derivative; 4 adamantylamino 6 hydrazinyl 1,3,5 triazin 2(1h) one; 4 cyclohexylamino 6 hydrazinyl 1,3,5 triazin 2(1h) one; 4 dimethylamino 6 hydrazinyl 1,3,5
DOI:
10.1016/j.tet.2014.07.058
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Affiliations Samara State Technical University, 244 Molodogvardeyskaya St., Samara, Russian Federation; Ural Federal University, 19 Mira St., Ekaterinburg, Russian Federation; I.Ya. Postovsky Institute of Organic Synthesis (Ural Branch of RAS), 22 S. Kovalevskaya St., Ekaterinburg, Russian Federation
Author Keywords Nitrogen heterocycles Cyclization Fused-ring systems Tautomerism Rearrangement
Funding Details Ministry of Education and Science of the Russian Federation
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Correspondence Address Parfenov, V.E.; Samara State Technical University, 244 Molodogvardeyskaya St., Russian Federation
Publisher Elsevier Ltd
CODEN TETRA
Language of Original Document English
Abbreviated Source Title Tetrahedron
Source Scopus