Synthesis, cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine and its hydrochloride salt

Molecules. 2012 Nov 8;17(11):13290-306. doi: 10.3390/molecules171113290.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemical synthesis
  • Adenine / chemistry
  • Calorimetry, Differential Scanning
  • Cyclization
  • Free Radicals / chemistry
  • Hydrolysis
  • Polymerization
  • Polynucleotides / chemical synthesis*
  • Polynucleotides / chemistry
  • Solubility
  • Solvents / chemistry
  • Spectroscopy, Fourier Transform Infrared
  • Sulfur Dioxide / chemistry
  • Thermogravimetry

Substances

  • 9-(2-diallylaminoethyl)adenine
  • 9-(2-diallylaminoethyl)adenine hydrochloride
  • Free Radicals
  • Polynucleotides
  • Solvents
  • Sulfur Dioxide
  • Adenine