Synthesis, Cyclopolymerization and Cyclo-Copolymerization of 9-(2-Diallylaminoethyl)adenine and Its Hydrochloride Salt

Molecules

Kamal H. Bouhadir¹  Lara Abramian¹  Alaa Ezzeddine¹  Karyn Usher¹ 

[1] ¹Department of Chemistry, American University of Beirut, Box 11-0236, Beirut, Lebanon ²Department of Chemistry, West Chester University, West Chester, PA 19383, USA ³Ashland Research Center, 500 Hercules Road, Wilmington, DE 19808, USA

关键词: polynucleotide analogs;    adenine;    cyclopolymerization;   

DOI  :  10.3390/molecules171113290

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.