Synthesis of (R)‐5‐(2′‐pentyl)barbituric acid derivatives of high optical purity | Zendy

Cook C. E. | Zendy; Tallent C. Ray | Zendy

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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.

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