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Some intramolecular michael additions of adenine derivatives
Author(s) -
Brahme Nanda M.,
Smith Walter T.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220128
Subject(s) - chemistry , acryloyl chloride , michael reaction , acrylate , intramolecular force , methyl acrylate , acrylic acid , polymer chemistry , solvent , organic chemistry , nucleic acid , addition reaction , copolymer , catalysis , polymer , biochemistry
In our attempts to prepare polymerizable derivatives of nucleic acid bases, we investigated the reaction of adenine ( 1 ) and 9‐(cyanoethyl)adenine ( 4 ) with acrylic anhydride and acryloyl chloride. Reactions of adenine with methyl acrylate and vinyl acrylate were also examined. The results show that these reactions are solvent dependent and the intermediate acryloyladenine 3 can undergo a facile intramolecular Michael reaction to form 7.