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Synthesis and spectroscopy of phosphonate derivatives of uracil and thymine. X‐ray crystal structure of diethyl 6‐uracilmethylphosphonate
Author(s) -
Ochocki Justyn,
Erxleben Andrea,
Lippert Bernhard
Publication year - 1997
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.5570340414
Subject(s) - chemistry , phosphonate , thymine , uracil , nuclear magnetic resonance spectroscopy , spectroscopy , crystal structure , medicinal chemistry , organic chemistry , dna , biochemistry , physics , quantum mechanics
A new class of phosphonate ligands, derived from uracil and thymine was designed, prepared and characterised. Dimethyl ( 4, 7 ) and diethyl ( 5, 8 ) uracilmethylphosphonates have been prepared by the reaction of chloromethyluracil isomers 2 and 3 with trimethyl phosphite and triethyl phosphite, respectively. The corresponding free acids, 5‐uracilmethylphosphonic acid 6 and 6‐uracilmethylphosphonic acid 9 , have also been isolated. The structure of the compounds has been assigned by nmr spectroscopy and, in the case of 8 , confirmed by X‐ray analysis.