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Further reactions of 3‐hydroxy‐1(3 H )‐isobenzofuranone with amines
Author(s) -
Sloan Kenneth B.,
Koch Suzanne A. M.
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.5570220242
Subject(s) - chemistry , alkylation , cytosine , prodrug , medicinal chemistry , organic chemistry , stereochemistry , catalysis , biochemistry , dna
The reaction of 3‐hydroxy‐1(3 H )‐isobenzofuranone (III) with 2‐phenylethylamines has been shown to give either monoalkylated VI or dialkylated VII products (prodrugs) depending on the number of equivalents of III used. The monoalkylated products disproprotionated to the dialkylated products unless they were stabilized as salts. In addition, the reaction of III with cytosine and adenine resulted in the formation of N 4 and N 6 ‐alkylated products, respectively. The alkylated 2‐phenylethylamines, and cytosine and adenine are representative of a new type of prodrug approach to modifying the physical chemical properties of these two important classes of drugs.