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Molecules 2012, 17(11), 13290-13306; doi:10.3390/molecules171113290
Article

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

1,* , 1, 1, 2 and 3
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.
Received: 11 September 2012 / Revised: 26 September 2012 / Accepted: 2 November 2012 / Published: 8 November 2012
(This article belongs to the Section Organic Synthesis)
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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 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.
Keywords: polynucleotide analogs; adenine; cyclopolymerization polynucleotide analogs; adenine; cyclopolymerization
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Bouhadir, K.H.; Abramian, L.; Ezzeddine, A.; Usher, K.; Vladimirov, N. Synthesis, Cyclopolymerization and Cyclo-Copolymerization of 9-(2-Diallylaminoethyl)adenine and Its Hydrochloride Salt. Molecules 2012, 17, 13290-13306.

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