- 8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide
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2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified.
- Bliman, David,Pettersson, Mariell,Bood, Mattias,Gr?tli, Morten
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p. 2929 - 2931
(2014/05/06)
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- The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination reactions of purines
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The microwave-assisted decomposition of DMF was thoroughly studied and the reaction conditions (temperature, solvent effect, and effect of additives, such as acids, bases, and salts) were optimized for its use in amination reactions. The applicability of this expedient methodology in purine chemistry and with various formamides is demonstrated.
- ?echová, Lucie,Jansa, Petr,?ála, Michal,Dra?ínsky, Martin,Holy, Antonín,Janeba, Zlatko
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experimental part
p. 866 - 871
(2011/03/19)
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- Effect of substituent structure on pyrimidine electrophilic substitution
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In an investigation into the electrophilic nitrosation reactions of a series of 4,6-disubstituted pyrimidine derivatives, a subtle interplay between the electronic nature of the C-4 and C-6 substituents and reactivity was found where these were chloro-, mono- or disubstituted amino groups. Effects such as the presence of an aryl group or two alkyl groups on the amino moiety impede the progress of the reaction despite the presence of a second activating group.
- van der Westhuyzen, Christiaan W.,Rousseau, Amanda L.,Parkinson, Christopher J.
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p. 5394 - 5405
(2008/01/07)
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- Mitsunobu reactions for the synthesis of carbocyclic analogues of nucleosides: Examintion of the regioselectivity
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In order to provide a general synthetic method for carbocyclic nucleosides, regioselectivities in Mitsunobu reaction of purine, pyrimidin-2-one and their substituted derivatives with a variety of alcohols with a variety of alcohols were examined and found to depend upon both substituents of the bases and kind of the alcohols.
- Toyota,Katagiri,Kaneko
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p. 1295 - 1305
(2007/10/02)
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- SYNTHESIS OF N,N,9-TRISUBSTITUTED ADENINES UNDER CONDITIONS OF PHASE-TRANSFER CATALYSIS
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Alkylation of N-mono- and N,N-disubstituted adenines by 2,6-dichlorobenzyl chlorides under the conditions of phase-transfer catalysis in the benzene-50percent aqueous sodium hydroxide system takes place regioselectively with the formation of the corresponding N,N,9-trisubstituted adenines (60-80percent).The isomeric N,N,3-trisubstituted adenines are also formed.The N,9-disubstituted adenines are alkylated regiospecifically under analogous conditions and give N,N,9-trisubstituted adenines with quantitative yields.
- Ramzaeva, N. P.,Gol'dberg, Yu. Sh.,Alksnis, E. R.,Lidak, M. Yu.,Shimanskaya, M. V.
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p. 1611 - 1615
(2007/10/02)
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- 9-Benzyl-6-(dimethylamino)-9H-purines with Antirhinovirus Activity
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A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B.The 9-benzylpurines that were unsubstituted in the 2-position had weak
- Kelley, James L.,Linn, James A.,Krochmal, Mark P.,Selway, J. W. T.
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p. 2001 - 2004
(2007/10/02)
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- 6-(Alkylamino)-9-benzyl-9H-purines. A New Class of Anticonvulsant Agents
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Several 9-alkyl-6-substituted-purines were synthesized and tested for anticonvulsant activity against maximal electroshock-induced seizures (MES) in rats.Most compounds were prepared in three steps from 5-amino-4,6-dichloropyrimidine or in two steps via alkylation of 6-chloropurine.Potent anticonvulsant activity against MES resided in compounds that contain a benzyl substituent at the 9-position of 6-(methylamino)- or 6-(dimethylamino)purine.Among commonly used agents for control of seizures, this type of structure represents a new class of potent anticonvulsant agents.
- Kelley, James L.,Krochmal, Mark P.,Linn, James A.,McLean, Ed W.,Soroko, Francis E.
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p. 606 - 612
(2007/10/02)
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- SYNTHESES OF N,N,3- AND N,N,9-TRIALKYLADENINES BY ALKYLATION OF N,N-DIYLKYLADENINES
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Alkylation of N,B,N-dimethyl- (Ia) and N,N-diethyladenine (Ib) with methyl iodide, ethyl iodide, and benzyl bromide in N,N-dimethylacetamide in the presence of potassium carbonate gave the corresponding N,N,9-trialkyladenines (II) in 54-74percent yields, as well as minor amounts of N,N,3-trialkyladenines (III).The alkylation of I without base gave the latter compounds (III) in 76-90percent yields.Keywords - N,N,3-tryalkyladenines: N,N,9-trialkyladenines; regioselective N-alykaltion; N,N-dialkyladenines; isomer ratio.
- Itaya, Taisuke,Matsumoto, Hiroo,Ogawa, Kazuo
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p. 1920 - 1924
(2007/10/02)
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