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Efficient N-Arylation and N-Alkenylation of the Five DNA/RNANucleobases

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  • Interdisciplinary Nanoscience Center
  • Institut for Kemi

A general approach to N-arylation and N-alkenylation of all five DNA/RNA nucleobases at the nitrogen atom normally attached to the sugar moiety in DNA or RNA has been developed. Various protected or masked nucleobases engaged readily in the copper-mediated Chan-Lam-Evans-modified Ullmann condensation with a range of different boronic acids at room temperature and were subsequently converted to the corresponding deprotected or unmasked adducts. Different N3-protecting groups were examined in the case of thymine, where the benzoyl group afforded the highest yields. A 4-alkylthio-substituted pyrimidin-2(1H)-one served as both a cytosine and a uracil precursor and was N-arylated and N-alkenylated in high yields. Adenine was efficiently and selectively N-arylated and N-alkenylated at the N9 position by employing a bis-Boc-protected adenine derivative, while a bis-Boc-protected 2-amino-6-chloropurine served as guanine precursor and could also be selectively N9-arylated and N9-alkenylated.

OriginalsprogEngelsk
TidsskriftJournal of Organic Chemistry
Vol/bind71
Nummer24
Sider (fra-til)9183-9190
Antal sider8
ISSN0022-3263
DOI
StatusUdgivet - 25 okt. 2006

Bibliografisk note

Paper id:: 10.1021/jo061694i

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