1257421-50-3Relevant academic research and scientific papers
A facile synthesis of novel acyclo-C-nucleoside analogues from L-rhamnose via variants of Bohlmann-Rahtz reaction
Kantevari, Srinivas,Putapatri, Siddamal Reddy
, p. 2251 - 2256 (2010)
Synthesis of a series of novel acyclo-C-nucleoside analogues bearing substituted pyridines, dihydro-6H-quinolin-5-ones, dihydro-5H-cyclopentapyridin- 5-one, tetrahydrocyclohepta[b] pyr-idine-5-one, and azafluorinone has been achieved in very good yields, through CeCl3·7H 2O-NaI-catalyzed one-pot condensation of a variant of the Bohlmann-Rahtz reaction using β-enaminones derived from l-rhamnose, acyclic and cyclic 1,3-dicarbonyls, and ammonium acetate. Ready availability of reactive β-enaminones, use of a cerium catalyst, and shorter reaction times are the advantages of this protocol over previous methodology. A plausible mechanism invoking cerium-catalyzed sequential Michael addition-cyclode- hydration-elimination reactions is also presented. Georg Thieme Verlag Stuttgart - New York.
