Physicochemical properties of some new 1,5- and 5,5-alkyl-substituted barbituric acids

The synthesis of six new barbituric acids 1b, 3a, 4b, 5, and 6b, including the novel 5-hydroxy derivative 3b, is reported together with spectroscopic data (proton magnetic resonance, ultraviolet, and infrared) for these and for five related known barbiturates for which such data is lacking. An interesting occurrence of non-equivalence of the N-1 and N-3 CH2(Et) protons in 3b is discussed.

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Dehydration of alcohols derived from 1-t-butyl-3-dimethylaminopropan-1-one; a novel cleavage reaction involving 2,6-dichlorobenzylmagnesium bromide

Canadian Journal of Chemistry ◽

10.1139/v70-166 ◽

1970 ◽

Vol 48 (6) ◽

pp. 1011-1013 ◽

Cited By ~ 2

Author(s):

A. F. Casy ◽

R. R. Ison

Keyword(s):

Magnetic Resonance ◽

Spectroscopic Data ◽

Proton Magnetic Resonance ◽

Tertiary Alcohol ◽

Cleavage Reaction ◽

Butyl Group ◽

Acid Catalyzed ◽

Cis And Trans

The acid-catalyzed dehydration of 1-t-butyl-3-dimethylamino-1-phenylpropan-1-ol gives cis(t-Bu/H)1-t-butyl-3-dimethylamino-1-phenylprop-1-ene exclusively. Dehydration of the product of reaction between 1-t-butyl-3-dimetnylammopropari-1-one and 2,6-dichlorobenzylmagnesium bromide gives cis and trans 2-t-butyl-1-2,6-dichlorophenyl-4-dimethylaminobut-2-ene plus the cis aminopropene of the first reaction. The formation of the aminopropene, together with that of its precursor tertiary alcohol, represents a novel cleavage reaction of 2,6-dichlorobenzylmagnesium bromide. The configurations of the aminoalkenes were established from proton magnetic resonance spectroscopic data, the cis(t-Bu/H)but-2-ene providing a further example of a magnetically non-equivalent t-butyl group.

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The novel temperature dependence of the proton magnetic resonance spectrum of the dioxouranium(VI)-NN-Dimethylformamide System

Journal of Magnetic Resonance (1969) ◽

10.1016/0022-2364(75)90071-2 ◽

1975 ◽

Vol 19 (2) ◽

pp. 243-244

Author(s):

Richard P Bowen ◽

Stephen F Lincoln ◽

Evan H Williams

Keyword(s):

Magnetic Resonance ◽

Temperature Dependence ◽

Proton Magnetic Resonance ◽

Resonance Spectrum ◽

Proton Magnetic Resonance Spectrum ◽

The Novel

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Studies of stereochemical influences upon anti-histaminic activity. The synthesis, configuration, and anti-histaminic properties of some isomeric aminobutenes

Canadian Journal of Chemistry ◽

10.1139/v69-061 ◽

1969 ◽

Vol 47 (3) ◽

pp. 423-427 ◽

Cited By ~ 6

Author(s):

A. F. Casy ◽

A. P. Parulkar

Keyword(s):

Double Bond ◽

Magnetic Resonance ◽

Spectroscopic Data ◽

Proton Magnetic Resonance ◽

Acid Catalyzed ◽

Related Compounds

The acid-catalyzed dehydration of 4-dimethylamino-2-p-methoxyphenyl-1-phenylbutan-2-ol yields all four possible 4-amino-1,2-diarylbutenes. Pure samples of each isomer have been isolated, double bond positions and configurations being established from proton magnetic resonance and ultraviolet spectroscopic data. A stereoselective route to cis aminobut-1-enes has been further investigated. The anti-histaminic properties of the reported butenes together with some related compounds are given and structural influences upon activity discussed.

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