Synthesis of 5‐/8‐Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolec­ular Chemistry. Issue 32 (1st October 2015)

• Record Type: Journal Article
• Authors: Bilbao, Nerea; Vázquez‐González, Violeta; Aranda, M. Teresa; González‐Rodríguez, David
• Is Part Of: European journal of organic chemistry. Issue 32(2015)
• Page Start: 7160
• Page End: 7175
• Publication Date: 2015-10-01
• Subjects: Supramolecular chemistry -- Self‐assembly -- Alkylation -- Cross‐coupling -- Nucleobases -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501026
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A series of lipophilic nucleobases that are substituted at the 5‐ (pyrimidines) or 8‐ (purines) position with either a halogen atom or a terminal triple bond have been synthesized. The sequences and reactions studied in this work, which mainly comprise halogenation, alkylation, Sonogashira coupling, and trimethylsilylacetylene deprotection, have been carefully optimized, to reach the final compounds in the most straightforward and convenient way, with the highest possible purity and yield. These compounds include cytosine, isocytosine, and uracil derivatives as pyrimidine heterocycles, and guanine, isoguanine, and 2‐aminoadenine derivatives as complementary purine bases. Variability was introduced at the N‐1/N‐9 positions of these pyrimidine/purine nucleobases, which were functionalized with alkyl or benzyl groups, as well as with protected amine or carboxylic acid substituents. The molecules prepared constitute a useful collection of synthetic intermediates for the field of chemical self‐assembly. Abstract : A series of lipophilic nucleobases substituted at the 5‐ (pyrimidines) or 8‐position (purines) with either a halogen atom or a terminal triple bond have been synthesized. These molecules comprise a useful collection of synthetic intermediates for the field of chemical self‐assembly.