Previous Article in event
Next Article in event
A New, Improved Synthesis of 9-Benzyladenine: An Important Heterocyclic Analogue of Adenosine Useful for Chemical and Biochemical Research of Nucleic Acids
Published: 01 November 1999 by MDPI in The 3rd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: 9-Benzyladenine (I) is a rare chemical often used by chemists, biochemists, as well as biophysical chemists doing research in the field of nucleic acids as a convenient heterocyclic base model for physicochemical comparison with adenosine. However, I is commercially unavailable, and the synthetic methods available from the literature are tedious and poor yielding. We have synthesized I from 5-amino-1-benzyl-4-cyanoimidazole (II) which, in turn, was synthesized from acyclic precursors, III, IV or V, using three different methods. We report herein all these methods, along with our recommendation for the best method in terms of both convenience and product yield to access both the imidazole precursor II and the target 9-benzyladenine (I).
Keywords: Improved Syntheses of 9-Benzyladenine and 5-Amino-4-cyano-1-benzylimidazole