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Synthesis of (R)‐5‐(2′‐pentyl)barbituric acid derivatives of high optical purity
Author(s) -
Cook C. E.,
Tallent C. Ray
Publication year - 1969
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.5570060210
Subject(s) - chemistry , barbituric acid , pulegone , pentobarbital , racemization , organic chemistry , secobarbital , thiamylal , malonic acid , medicinal chemistry , stereochemistry , chromatography , medicine , essential oil , toxicology , biology
Natural (R)‐(+)‐pulegone ( 1 ) was converted to 3‐methylhexanoic acid ( 4 ) by a sequence which precluded racemization. Conversion of this to malonic esters 8 , 5 , and 11 permitted the synthesis of pentobarbital ( 6 ) secobarbital ( 12 ), thiopental ( 9 ), thiamylal(10 ), and 5‐(2′‐pentyl)barbituric acid ( 7 ), all having the ( R )‐configuration in the side chain.