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
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)
Download PDF [747 KB, uploaded 18 June 2014]
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
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
Scifeed alert for new publications
Never miss any articles matching your research from any publisher- Get alerts for new papers matching your research
- Find out the new papers from selected authors
- Updated daily for 49'000+ journals and 6000+ publishers
- Define your Scifeed now
Share & Cite This Article
MDPI and ACS Style
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.
Related Articles
Article Metrics
Comments
Molecules
EISSN 1420-3049
Published by MDPI AG, Basel, Switzerland
RSS
E-Mail Table of Contents Alert