Synthesis, cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine and its hydrochloride salt

• Published in: Molecules (Basel, Switzerland) Vol. 17; no. 11; pp. 13290 - 13306
• Main Authors: Bouhadir, Kamal H, Abramian, Lara, Ezzeddine, Alaa, Usher, Karyn, Vladimirov, Nikolay
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 08.11.2012; MDPI
• Subjects: adenine; Adenine - analogs & derivatives; Adenine - chemical synthesis; Adenine - chemistry; Aqueous solutions; Calorimetry, Differential Scanning; Cyclization; cyclopolymerization; Free Radicals - chemistry; Hydrolysis; Molecular weight; Polymerization; Polymers; polynucleotide analogs; Polynucleotides - chemical synthesis; Polynucleotides - chemistry; Quantum dots; Solubility; Solvents - chemistry; Spectroscopy, Fourier Transform Infrared; Sulfur Dioxide - chemistry; Thermogravimetry; United States > US
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules171113290

We report herein the synthesis and characterization of 9-(2-diallylaminoethyl) adenine. We evaluated two different synthetic routes starting with adenine where the optimal route was achieved through coupling of 9-(2-chloroethyl)adenine with diallylamine. The cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine hydrochloride salt resulted in low molecular weight oligomers in low yields. In contrast, 9-(2-diallylaminoethyl)adenine failed to cyclopolymerize, however, it formed a copolymer with SO₂ in relatively good yields. The molecular weights of the cyclopolymers were around 1,700-6,000 g/mol, as estimated by SEC. The cyclo-copolymer was stable up to 226 °C. To the best of our knowledge, this is the first example of a free-radical cyclo-copolymerization of a neutral alkyldiallylamine derivative with SO₂. These polymers represent a novel class of carbocyclic polynucleotides.