Central nervous system active compounds. III. The synthesis of 4- and 6-substituted caprolactam derivatives by the Schmidt and Beckmann rearrangements

1980 ◽  
Vol 33 (11) ◽  
pp. 2477 ◽  
Author(s):  
GI Hutchison ◽  
RH Prager ◽  
AD Ward
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Beckmann Rearrangement ◽  
Active Compounds ◽  
System Activity ◽  
Nervous System Activity ◽  
Central Nervous System Activity ◽  
The Central Nervous System

The synthesis is described of hexahydroazepin-2-ones (caprolactams) bearing 1-4 alkyl or aryl groups at C4 and C6 by the Beckmann or Schmidt reactions on the corresponding cyclohex-2-enone. Further evidence for the mechanism of the Beckmann rearrangement of these unsaturated oximes is advanced. The central nervous system activity of the alkylated caprolactams is reported.

Central-Nervous-System Active Compounds .XVI. Some Chemistry of 6-Oxo Caprolactams Derived From an Enamine Ring-Expansion Synthesis

1985 ◽  
Vol 38 (12) ◽  
pp. 1847 ◽  
Author(s):  
GW Heinicke ◽  
AM Morella ◽  
J Orban ◽  
RH Prager ◽  
AD Ward
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Ring Expansion ◽  
Enol Form ◽  
Dimethyl Acetylenedicarboxylate ◽  
Active Compounds ◽  
Keto Ester ◽  
System Activity ◽  
Nervous System Activity ◽  
Central Nervous System Activity

Several 6-oxo caprolactam derivatives have been prepared by the ring- expansion of enaminopyrrolidones with dimethyl acetylenedicarboxylate . Other acetylenic systems did not react. The products exist in the enol form of the β- keto ester system are are very resistant towards hydrolysis. They react with hydrazine and phenylhydrazine to form pyrazolo [3,4-c] azepinones in low yield. Many of the caprolactams and their pyrazolo -fused derivatives show central nervous system activity of a depressant nature in mice.

Central nervous system active compounds. VIII. New syntheses of phthalide isoquinolines

1981 ◽  
Vol 34 (5) ◽  
pp. 1085 ◽  
Author(s):  
RH Prager ◽  
JM Tippett ◽  
AD Ward
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Active Compound ◽  
Sodium Methoxide ◽  
Direct Coupling ◽  
Sodium Cyanoborohydride ◽  
Active Compounds ◽  
System Activity ◽  
Nervous System Activity ◽  
Central Nervous System Activity

Isoquinoline methiodides react with phthalides in the presence of sodium methoxide to give intermediates which may be reduced to phthalide isoquinolines with hydrogen or sodium cyanoborohydride. The predominant isomer formed is the erythro, which is also the more active compound when tested for central nervous system activity. The direct coupling of phthalides with dihydroisoquinoline methiodides under these conditions fails to occur.

Central nervous system active compounds. II. The synthesis of some 4-, 5-, 6- and 7-substituted caprolactams

1976 ◽  
Vol 29 (12) ◽  
pp. 2667 ◽  
Author(s):  
T Duong ◽  
RH Prager ◽  
JM Tippett ◽  
AD Ward ◽  
DIB Kerr
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Alkyl Aryl ◽  
Active Compounds ◽  
System Activity ◽  
Substituent Group ◽  
Nervous System Activity ◽  
Central Nervous System Activity ◽  
Synthetic Approaches

The synthesis of caprolactam derivatives substituted at C4, C5, C6 and C7 with alkyl, aryl, acyl and hetero substituents is described. A variety of synthetic approaches to these compounds have been investigated and assessed, particularly for the synthesis of C4- and C6-substituted compounds. A significant number of the C4-, C6- and C7- substituted compounds prepared show central nervous system activity, ranging from convulsants to depressants depending on the position and nature of the substituent group.

Central nervous system active compounds. IX. Cinnolinylisobenzofuranones [1-(3-Phthalidyl)cinnolin-4(1H)-ones]

1981 ◽  
Vol 34 (12) ◽  
pp. 2619 ◽  
Author(s):  
PA Marshall ◽  
BA Mooney ◽  
RHWAD Prager
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Sodium Salt ◽  
Active Compounds ◽  
System Activity ◽  
Nervous System Activity ◽  
Spectral Evidence ◽  
Central Nervous System Activity ◽  
Infrared Spectral ◽  
Moderate Yield

The synthesis and central nervous system activity of a number of cinnolinylisobenzofuranones are described. The compounds are prepared in moderate yield by the reaction of the sodium salt of a cinnolin-4-one with the appropriate 3-bromophthalide. 1H, 13C n.m.r., and infrared spectral evidence for the structure of the compounds is presented. The compounds cause a loss of muscular control in mice.

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