294202-82-7Relevant articles and documents
Preparation of N-(alk-1-enyl) nucleobase compounds by Horner and Horner-Wadsworth-Emmons reactions
Boesen, Thomas,Madsen, Christian,Henriksen, Ulla,Dahl, Otto
, p. 2015 - 2021 (2007/10/03)
A series of new N9-(alk-1-enyl)adenines and N1-(alk-1-enyl)thymines has been prepared by Homer reactions of the new phosphine oxides N9 -(diphenylphosphorylmethyl)adenine and N1-(diphenylphosphorylmethyl)thymine derivatives 13a-c, or Horner-Wadsworth-Emmons reactions of the corresponding new phosphonates 14a-b, with benzaldehyde and various ketones. Yields were highest for the Homer reactions (10-79%), and were limited by steric hindrance, enolization of the ketones, and decomposition of some of the N1-(alk-1-enyl)thymines in the presence of excess base (NaH). Butanal gave mixtures of products under Homer conditions, probably because aldol reactions intervened.