title: Convenient and efficient syntheses of N(6)- and N(4)- substituted adenines and cytosines and their 2'-deoxyribosides.
abstract: Convenient and efficient methods of the synthesis of N(6)- and N(4)-substituted derivatives of adenine and cytosine and their 2'-deoxyribosides were developed. The reactions of either unprotected nucleobases (adenine, cytosine) or unprotected 2'-deoxyribosides with aryl or alkyl aldehydes give corresponding Schiff bases that can be reduced to the target title compounds with high overall yields. In the case of aryl aldehydes the imine derivatives are obtained in the presence of methoxides in methanol and reduced with sodium borohydride. The corresponding reactions with alkyl aldehydes require the use of acetic acid and borane dimethyl sulfide complex instead.
authors.affiliation: Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland.
authors.forename: Ewelina
authors.initials: E
authors.lastname: Adamska
authors.forename: Jan
authors.initials: J
authors.lastname: Barciszewski
authors.forename: Wojciech T
authors.initials: WT
authors.lastname: Markiewicz
mesh_terms: D000225:Adenine / Q000138:chemical synthesis* / Q000737:chemistry; D003596:Cytosine / Q000138:chemical synthesis* / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009690:Nucleic Acid Conformation
chemical_list: D003853:Deoxyribonucleosides; D003596:Cytosine; D000225:Adenine