Vinyl polymerization. 217. Vinyl compounds of nucleic acid basis. I. Synthesis of N‐vinylthymine, and N‐vinyladenine

Abstract

The synthesis of N-vinyluracil, N-vinylthymine, and N-vinyladenine is described. The general procedure consists of the conversion of the corresponding nucleic acid bases t o their N-hydroxyethyl compounds, followed by chlorination to N-chloroethyl compounds and dehydrochlorination to the N-vinyl derivatives. ZUSAMMENFASSUNG:Die Synthese van N-Vinyluracil, N-Vinylthymin sowie N-Vinyladenin wilrde beschrieben. Diese drei N-Vinylverbindungen wurden ausgehend van den entsprechenden Nucleinsaurebasen iiber die N-Hydroxyathylderivate und die durch Chlorierung erhaltenen N-Chlorathylderivate dargestellt. * ) 216. of the series: K. TAKEMOTO, M. IZUBAYASHI, and M. IMOTO, Makromolekulare Chem. 119 (1968) 147 (Nr. 2825).

Structure of 9-(2-hydroxyethyl)guanine

“…The yield of 9-(2-hydroxyethyl)guanine was rather low in the reaction reported by Yamazaki (1969). We applied a simple reaction after Ueda, Kondo, Kono, Takemoto & Imoto (1968); reaction of 2-N-acetylguanine with ethylene carbonate in dimethyl sulfoxide at 403 K in the presence of a trace of sodium hydroxide yielded both 9-substituted and 7-substituted derivatives. When N,N-dimethyl-4-pyridylamine was used instead of sodium hydroxide, the deacetylated 9-substituted derivative was obtained by isolation and purification on porous resin column.…”

Structure of 1-(2-hydroxyethyl)cytosine

“…1-(2-Hydroxyethyl)cytosine, synthesized from cytosine and ethylene carbonate in dimethylformamide in the presence of a trace of sodium hydroxide (Ueda, Kondo, Kono, Takemoto & Imoto, 1968 was evaluated by counting statistics and q estimated to be 2.59 × 10 -5 from measurement of monitored reflexions (McCandlish & Stout, 1975 (Takenaka & Sasada, 1980), DCMS82 (Takenaka & Sasada, 1982a) and LISTUP . Final atomic parameters are given in Table 1.…”

Functional Monomers and Polymers CXXII. Synthesis of Polymethacrylates Containing Nucleic Acid Bases and Their Methylated Derivatives by Copolymerization

“…16 9-(2-M ethacryloyloxyethyl) adenine (9) (MAOA): The reaction of compound 8 with methacrylic anhydride in dimethylformamide gave the methacrylate monomer 9. 16 1-Methyl-9-( 2-hydroxyethyl)adenine (10): To a solution of 9-(2-hydroxyethyl)adenine (8) (lOg, 0.056mol) in dimethylformamide (400 ml), methyl iodide (10 ml, 0.16 mol) was added, and the solution was stirred for 12 h at room temperature. Methyl iodide (5 ml, 0.08 mol) was further added to the solution which was stirred for an additional 12 h at room temperature.…”

“…16 From compound 8 with methacrylic anhydride, MAOA (9) was prepared. 16 Alternatively, monomer 9 can be prepared by a reaction of 2-bromoethyl methacrylate with sodium salt of adenine. 17 The methylation of 9-(2-hydroxyethyl)-adenine (8) was carried out using methyl iodide in dimethylformamide at room temperature to give 1-methyl-9-(2-hydroxyethyl)-adenine as iodide salt (10).…”