25491-56-9Relevant articles and documents
'Reductive Heck reaction' of 6-halopurines
Tobrman, Tomá?,Dvo?ák, Dalimil
, p. 273 - 276 (2004)
Alkenylation of 9-benzyl-6-halopurines with alkenes does not proceed under conventional Heck conditions. However, in the presence of triethylammonium formate a mixture of the corresponding saturated products was obtained. In contrast to the classical Heck reaction, the regioselectivity of this process is low giving a mixture of both α- and β-products regardless of the electronic nature of the substituent on the double bond of the alkene.
Microwave promoted reaction of purin-6-yl magnesium halides with aldehydes in dichloromethane at 100u202f°C
Gordon, Malcolm R.,Lindell, Stephen D.
, p. 1945 - 1947 (2018)
Treatment of a dichloromethane solution of 9-benzyl or 9-phenyl 6-iodopurine with ethereal ethylmagnesium bromide at ambient temperature gives the corresponding purin-6-yl magnesium halides. Addition of an aldehyde followed by heating at 100 °C in a microwave reactor yielded the corresponding carbinols in 52–81% yield.
The synthesis of nebularine and its analogs via oxidative desulfuration in aqueous nitric acid
Xia, Ran,Sun, Li-Ping,Qu, Gui-Rong
, p. 88 - 91 (2016/12/24)
The synthesis of nebularine and its analogs has been achieved via oxidative desulfuration in H2O for the first time. With 50% HNO3as an oxidant and solvent, 18 products were obtained in good yields (70%–94%). The oxidative desulfuration system could tolerate different functional groups including fluoro, chloro, amino, alkyl, allyl, ribosyl, deoxyribosyl, and arabinofuranosyl groups.More importantly, the drug nebularine could be obtained successfully on a 20 g scale, which made this route more attractive for industrial applications.
Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water
Xia, Ran,Xie, Ming-Sheng,Niu, Hong-Ying,Qu, Gui-Rong,Guo, Hai-Ming
, p. 1077 - 1081 (2014/03/21)
A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66-95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.
A method for the reductive scission of heterocyclic thioethers
Graham, Thomas H.,Liu, Wensheng,Shen, Dong-Ming
supporting information; experimental part, p. 6232 - 6235 (2012/01/03)
A mild, chemoselective, and generally high-yielding method for the reductive scission of heterocyclic thioethers is described. Suitable heterocycles have a thioether substituent at the 2-position relative to a ring heteroatom. The convenient and straightforward method is demonstrated with reactants which are not compatible with the standard Raney nickel conditions such as sulfides, sulfones, and thiophenes. In addition, benzyl esters, benzyl amides, and benzyl carbamates are tolerated by the reductive reaction conditions.
Selective synthesis of 7-substituted purines via 7,8-dihydropurines
Kotek, Vladislav,Chudikova, Nadezda,Tobrman, Tomas,Dvorak, Dalimil
, p. 5724 - 5727 (2011/03/19)
A simple and efficient protocol for the preparation of 7-substituted purines is described. 6- and 2,6-Dihalopurines were N9-tritylated and then transformed to 7,8-dihydropurines by DIBAL-H. Subsequent N 7-alkylation followed by N9-trityl deprotection with trifluoroacetic acid was accompanied by spontaneous reoxidation, which led to the 7-substituted purines at 55 - 88% overall isolated yields.
DIKETO ACIDS WITH NUCLEOBASE SCAFFOLDS: ANTI-HIV REPLICATION INHIBITORS TARGETED AT HIV INTEGRASE IN COMBINATION THERAPY
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Page/Page column 64-65, (2008/06/13)
A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HIV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HFV and in the treatmen
Diketo acids with nucleobase scaffolds: anti-HIV replication inhibitors targeted at HIV integrase
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Page/Page column 22, (2008/06/13)
A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HIV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HIV and in the treatmen
Diketo acids on nucleobase scaffolds as inhibitors of Flaviviridae
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Page/Page column 22, (2010/11/24)
A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HCV replication through inhibition of HCV NS5B RNA polymerase, is described. These compounds are useful in the prevention or treatment of infection by HCV and in th
Nucleic acid related compounds. 136. Synthesis of 2-amino- and 2,6-diaminopurine derivatives via inverse-electron-demand Diels-Alder reactions
Lin, Xiaoyu,Robins, Morris J.
, p. 1029 - 1041 (2008/02/07)
Thermal inverse-electron-demand Diels-Alder reactions of 5-aminoimidazoles and 2,4,6-tris-(ethoxycarbonyl)-1,3,5-triazine (2) with spontaneous retro-Diels-Alder loss of ethyl cyanoformate and elimination of ammonia give 2,6-bis(ethoxycarbonyl)purines. A report that selective alkaline hydrolysis followed by acid-catalyzed decarboxylation gave 6-(ethoxycarbonyl)purine products was not in harmony with known reactions in purine chemistry. Our reinvestigation has shown that the 6-(ethoxycarbonyl) group undergoes preferential base-promoted hydrolysis, as expected, but regioselectivity for attack of hydroxide at the carbonyl group at C6 is not high (relative to hydrolysis of both C2 and C6 esters). The structure of 9-benzyl-2- (ethoxycarbonyl)purine was determined by X-ray crystallography and confirmed by Curtius rearrangement of the azidocarbonyl analogue to give 2-amino-6- benzylpurine. Acid-catalyzed decarboxylation of the 2,6-dicarboxylate formed during hydrolysis gave 9-benzylpurine, and Curtius rearrangement of 2,6-bis(azidocarbonyl)-9-benzylpurine gave 2,6-diamino-9-benzylpurine. Attempted applications of inverse-electron-demand Diels-Alder reactions of 2 with nucleoside derivatives were problematic.
