Template atom transfer radical polymerization of a diaminopyrimidine‐derivatized monomer in the presence of a uracil‐containing polymer

Uracil‐derivatized monomer 6‐undecyl‐1‐(4‐vinylbenzyl)uracil and diaminopyrimidine‐derivatized monomer 2,6‐dioctanoylamido‐4‐methacryloyloxypyrimidine (DMP) were synthesized and polymerized by atom transfer radical polymerization (ATRP). A well‐defined, highly soluble, uracil‐containing polymer, poly[6‐undecyl‐1‐(4‐vinylbenzyl)uracil] (PUVU), was prepared in dioxane at 90 °C with CuBr/1,1,4,7,10,10‐hexamethyltriethylenetetramine as the catalyst and methyl α‐bromophenylacetate as the initiator. PUVU was further used as a template for the ATRP of DMP. The enhanced apparent rate constant of the DMP polymerization in the presence of PUVU indicated that the ATRP of DMP occurred along the PUVU template. The template polymerization produced a stable and insoluble macromolecular complex, PUVU/poly(2,6‐dioctanoylamido‐4‐methacryloyloxypyrimidine). An X‐ray diffraction study confirmed that the complex had strandlike domains. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 6607–6615, 2006     

Synthesis and new rearrangements of 4-isoxazolin-4,5-dicarboxylic acid derivatives

Acyclic nitrones react with dimethyl acetylenedicarboxylate (DMAD) to give stable isoxazolines, from which the ones that contain electron-donating aromatic rings at the C3 position (R¹) were shown to undergo unprecedented fragmentation at room temperature, giving the R¹-aldehyde and inseparable product mixtures, probably due to the formation of highly reactive species such as iminocarbenes. Attempts to convert the isoxazolines to the corresponding stable azomethine ylides, by refluxing in toluene, again led to the same product mixtures as above (e.g., the room temperature decomposition). Isoxazolines when reacted with methoxide at room temperature afforded highly functionalised diastereomeric mixtures. Also, isoxazolines, when reacted with propylamine, gave the corresponding amides regioselectively, all of which were more stable than the parent isoxazolines.     

Three-component catalytic method for synthesis of α-amino phosphonates with the use of α-amino acids as amine component

Interaction of aliphatic and aromatic aldehydes and ketones with optically active L-α-amino acids or their esters in the three-component catalytic one-pot synthesis of α-aminophosphonates was studied. The corresponding α-amino phosphonates are formed in high yields as mixtures of diastereomers. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 768–774, April, 2007.     

An Efficient Synthesis of 8-Amino-9-Benzylguanine

The reaction of 2,5-diamino-4-benzylamino-pyrimidin-6(III)-one (6) with benzoyl isothiocyanate furnished 2-amino-4-benzylamino-5-[1-(3-benzoylthioureido)]-pyrimidin-6(1H)-one (7) in good yield. The title compound I was synthesized from compound 7 via a cyclodesulfurative reaction with DCC in DMF at 80°C directly to form 8-benzoylamino-9-benzylguanine (9) which was subsequently treated with 1 N sodium hydroxide.     

Stereoselective synthesis of (Z)-γ-cyano-β-perfluoroalkyl-β,γ-unsaturated esters

(Z)-γ-Cyano-β-perfluoroalkyl-β,γ-unsaturated esters have been synthesized by the reaction of perfluoroacylated phosphonates with organozinc reagent in 50-71% (three steps) yields.     

NMR spectroscopy of organophosphorus compounds II: Stereochemistry of [1-(2H-azirin-2-yl)alkyl]phosphonates

Summary The conformation and relative configuration of [1-(2H-azirin-2-yl)alkyl]phosphonates (2) has been established by thorough investigation of some characteristic representatives of the series by¹H,¹³C,¹⁵N, and³¹P NMR spectroscopy. It is shown that the chemical shift of the proton located to the phosphonate group can be used as a criterion for the discrimination and stereochemical assignment of diastereoisomers. NMR spectroscopic features of the compounds are discussed in terms of structural relationships.Dedicated to Univ.-Prof. Dr.K. Schlögl with the best wishes to his 70^th birthday     

Facile synthesis of acyclic azanucleosides from N-pivaloyloxymethyl amides and sulfonamides: synthesis of aza-analogues of Ganciclovir

N-Pivaloyloxymethyl amides and sulfonamides, readily available from N-alkylation of both amides and sulfonamides with commercial chloromethyl pivaloate, were converted into acyclic azanucleosides via a one-pot base silylation/nucleoside coupling procedure.     

Pulse radiolysis of one-electron oxidation of rare tricyclic nucleoside derivative

~~Pulse radiolysis of one-electron oxidation of rare tricyclic nucleoside derivative@赵红卫$Shanghai Institute of Nuclear Research, Chinese Academy of Sciences! Shanghai 201800,China @江致勤$Department of Chemistry, Tongji Unviersity!Shanghai 200092,China @窦大营$Shanghai Institute of Nuclear Research, Chinese Academy of Sciences! Shanghai 201800,China @吴铁一$Shanghai Institute of Nuclear Research, Chinese Academy of Sciences! Shanghai 201800,China @王文锋$Shanghai…