Tetrahedron p. 1893 - 1904 (1985)
Update date:2022-08-04
Topics:
Odijk, W. M.
Koomen, G. J.
Fluorescent pyrido<2,1-i>purines 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 pyrido<2,1-i>purines into the corresponding ribosides protection against nucleophilic attack was necessary.
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Doi:10.1016/S0040-4039(00)84115-5
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(1985)