synthesis, cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine and its hydrochloride salt合成、环聚合和cyclo-copolymerization 9 -盐酸(2-diallylaminoethyl)腺嘌呤和盐.pdfVIP

Molecules 2012, 17, 13290-13306; doi:10.3390/molecules171113290 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis, Cyclopolymerization and Cyclo-Copolymerization of 9-(2-Diallylaminoethyl)adenine and Its Hydrochloride Salt Kamal H. Bouhadir 1,*, Lara Abramian 1, Alaa Ezzeddine 1, Karyn Usher 2 and 3 Nikolay Vladimirov 1 Department of Chemistry, American University of Beirut, Box 11-0236, Beirut, Lebanon 2 Department of Chemistry, West Chester University, West Chester, PA 19383, USA 3 Ashland Research Center, 500 Hercules Road, Wilmington, DE 19808, USA * Author to whom correspondence should be addressed; E-Mail: kb05@.lb; Tel.: +961-01-350-000; Fax: +961-01-365-217. Received: 11 September 2012; in revisedform: 26 September 2012 / Accepted: 2 November 2012 / Published: 8 November 2012 Abstract: 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