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

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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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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