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The synthesis of biologically relevant 4(5)‐phosphono‐5(4)‐aminoimidazoles using a Pd‐catalyzed coupling reaction
Author(s) -
Lin Jing,
Thompson Charles M.
Publication year - 1994
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.5570310672
Subject(s) - chemistry , curtius rearrangement , moiety , palladium , triphenylphosphine , catalysis , coupling reaction , purine , hydrolysis , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , enzyme
Regiochemically defined 1‐benzyl‐4‐phosphono‐5‐carboalkoxyimidazoles were synthesized from the corresponding 4‐bromoimidazoles using a tetrakis(triphenylphosphine)palladium(0)‐catalyzed coupling reaction with diethyl phosphite. The corresponding Michaelis‐Arbusov reaction failed to give a phospho‐nylated product. The carbomethoxy moiety was converted to an amino group using a Curtius rearrangement to afford 1‐benzyl‐4‐phosphono‐5‐amino‐imidazoles. Following deprotection and hydrolysis, phos‐phonic acid‐linked aminoimidazoles were accessed that resemble intermediates formed during purine biosynthesis.