SYNTHESIS OF (R)-5-(2'-PENTYL)BARBITURIC ACID DERIVATIVES OF HIGH OPTICAL PURITY

被引：24

作者：

COOK, CE

TALLENT, CR

机构：

[1] Chemistry and Life Sciences Laboratory, Research Triangle Institute, North Carolina, 27709, Research Triangle Park

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1969年 / 6卷 / 02期

关键词：

D O I：

10.1002/jhet.5570060210

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Natural (R)‐(+)‐pulegone (1) was converted to 3‐methylhexanoic acid (4) by a sequence which precluded racemization. Conversion of this to malonic esters8, 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. Copyright © 1969 Journal of Heterocyclic Chemistry

引用

页码：203 / &

共 24 条

[1]

Abe K., 1955, J PHARM SOC JPN, V75, P891

[2] A STUDY OF SYNTHESIS OF BARBITURATES IN DIMETHYL SULFOXIDE SOLVENT [J].

BERES, JA ;

PEARSON, DE ;

BUSH, MT .

JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (06) :1078-&

[3]

CARROLL FI, IN PRESS

[4] BRANCHED-CHAIN FATTY ACIDS .16. SYNTHESIS OF THE OPTICAL ISOMERS OF 15-METHYLOCTADECANOIC ACID [J].

CASON, J ;

COAD, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (10) :4695-4697

[5]

CRABBE P, 1965, OPTICAL ROTATORY DIS, P77

[6] THE CONFIGURATIONS OF THE 3-METHYLCYCLOPENTANONES AND RELATED COMPOUNDS [J].

EISENBRAUN, EJ ;

MCELVAIN, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (12) :3383-3384

[7] SYNTHESIS OF ALKYLMALONIC ESTERS BY OXALATE CONDENSATIONS [J].

FLOYD, DE ;

MILLER, SE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (10) :2354-2355

[8]

FREDGA A, 1941, ARKIV KEMI MIN GEO B, V14

[9]

FREDGA A, 1942, ARKIV KEMI MIN GEO B, V15

[10] THE EMPLOYMENT OF SODIUM HYDRIDE AS A CONDENSING AGENT [J].

GREEN, N ;

LAFORGE, FB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (06) :2287-2288

← 1 2 3 →