100109-28-2Relevant academic research and scientific papers
FLUORESCENT NUCLEOSIDE ANALOGUES. SYNTHESIS OF FLUORESCENT PYRIDOPURINES, AND THEIR CORRESPONDING RIBOSIDES
Odijk, W. M.,Koomen, G. J.
, p. 1893 - 1904 (1985)
Fluorescent pyridopurines can in principle be obtained via Michael-addition of a suitable anion of a purine derivative to an acetylenic ester, followed by based-catalyzed cyclization, as depicted in Scheme II. 6-Substituted purine-derivatives are obtained via nucleophilic substitution on 6-chloro- and 6-methylsulfonylpurine (8a and 8b).In the presence of methyl propiolate and sodium methoxide, before cyclization, two consecutive Michael-additions take place, leading to 13 and 14.With substituted acetylenic esters, cyclization occurs after one Michael-addition. Michael-additions with ethylenic esters did not lead to expected cyclization products, except in cases where oxidation took place.For the conversion of the pyridopurines into the corresponding ribosides protection against nucleophilic attack was necessary.
