- Alkoxy base-mediated selective synthesis and new rearrangements of 1,2,4-triazolodipyrimidinones
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A versatile approach for the synthesis of [1,2,4]triazolodipyrimidinones with various annulations of the triazole and pyrimidine rings was developed. The isomeric triazolodipyrimidinones were obtained by the stepwise condensation of partially hydrogenated
- Pyatakov, Dmitry A.,Astakhov, Alexander V.,Sokolov, Andrey N.,Fakhrutdinov, Artem N.,Fitch, Andrew N.,Rybakov, Victor B.,Chernyshev, Vladimir V.,Chernyshev, Victor M.
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p. 748 - 754
(2017/03/31)
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- Partially hydrogenated 2-amino[1,2,4]triazolo[1,5-a]pyrimidines as synthons for the preparation of polycondensed heterocycles: Reaction with chlorocarboxylic acid chlorides
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Partially hydrogenated 2-amino[1,2,4]triazolo[1,5-a]pyrimidines and 2-amino[1,2,4]triazolo[5,1-b]quinazolines react with the chlorides of chloroacetic, 3-chloropropanoic, and 4-chlorobutanoic acids at 0-5 C to give amides through acylation of the 2-amino group. Heating the corresponding 3-chloropropanoyl derivatives at 80-90 C in DMF leads to selective intramolecular alkylation at N-3 to form the chlorides of partially hydrogenated [1,2,4]triazolo[1,5-a:4,3-a′]dipyrimidin-5-ones and pyrimido[2′, 1′:3,4][1,2,4]triazolo[5,1-b]quinazolin-12-ones. It may be more convenient to prepare such compounds through one-pot processes. Some reactions of the synthesized chlorides of polycondensed heterocycles have been studied. Conditions have been found to effect the selective synthesis of free bases, oxidative aromatization or hydrolysis of the dihydropyrimidine cycle, and the selective hydrolytic cleavage or elimination of the pyrimidone ring. Some of the resulting compounds represent new mesoionic heterocycles.
- Chernyshev, Victor M.,Pyatakov, Dmitry A.,Sokolov, Andrey N.,Astakhov, Alexander V.,Gladkov, Eugene S.,Shishkina, Svetlana V.,Shishkin, Oleg V.
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p. 684 - 701
(2014/02/14)
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- Improved synthesis of 2-amino-1,2,4-triazolo[1,5-a]pyrimidines
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An improved procedure is suggested for preparing 2-amino-1,2,4-triazolo[1, 5-a]pyrimidines from 3,5-diamino-1,2,4-triazole and unsaturated aromatic ketones, with acetyl protection of the amino group in the step of oxidation of 2-amino-4,7-dihydro-1,2,4-tr
- Chernyshev,Sokolov,Taranushich
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p. 1134 - 1137
(2008/02/05)
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- CYCLOCONDENSATION OF CHALCONES WITH DI- AND TRIAMINO-1,2,4-TRIAZOLES
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We have carried out the synthesis of 2-amino-5,7-diaryl-1,2,4-triazolopyrimidines from chalcones and 3,4,5-triamino-1,2,4-triazole and synthesized them independently via the 4,7-dihydro derivatives.The course and mechanism of the cyclocondensation
- Desenko, S. M.,Kolos, N. N.,Tueni, M.,Orlov, V. D.
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p. 782 - 784
(2007/10/02)
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