10.1002/hlca.19800630641
The research explored the 1,3-dipolar additions to 7-methylthieno[2,3-c]pyridine 1,1-dioxide. The study aimed to investigate the influence of the condensed pyridine ring on the orientation of the addition and the stability of the resulting primary products. Various 1,3-dipoles, including diazomethane, diazoethane, ethyl diazoacetate, phenyldiazomethane, and phenyl azide, were reacted with the target compound. The primary products were characterized using spectroscopic techniques, and their behavior under elevated temperatures and basic conditions was examined. The findings revealed that these products could undergo transformations such as loss of SO2 or N2 under certain conditions, leading to the formation of different compounds like pyrazoles and cyclopropanes.
10.1021/jm00328a005
The research focuses on the synthesis and study of 2-phenoxycyclopropylamines, which are of interest due to their potential as monoamine oxidase (MAO) inhibitors. The synthesis process begins with the reaction between phenyl vinyl ether and ethyl diazoacetate in the presence of copper to produce ethyl 2-phenoxycyclopropanecarboxylate. This ester is then hydrolyzed to yield the corresponding acid, which can exist in cis and trans forms. The researchers were able to separate and characterize these isomers, with the trans form being more thermodynamically stable and produced in greater yield. The esters were further converted into hydrazides, which underwent the Curtius degradation to yield amines. The amines were obtained as colorless liquids and their properties were studied. The research also involved testing the MAO inhibitory activity of these compounds in vivo and in vitro, with findings indicating no consistent difference in activity between the cis and trans forms. Additionally, the duration of action, acute toxicity, and other pharmacological properties of the trans-2-phenoxycyclopropylamine were investigated.
10.1021/jm00396a014
This research aimed to synthesize and test N,N-dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine for their activity as central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor agonists. The study found that a hydroxy substituent in the 2- or 3-position of the phenyl ring was necessary for 5-HT-receptor stimulation, with N,N-diethyl or N,N-di-n-propyl substitution yielding the most potent 5-HT-receptor agonists. Notably, the 4-hydroxy and 3,4-dihydroxy derivatives were inactive at central DA and 5-HT receptors. The compounds were synthesized using various chemical reactions, including cyclopropanation, Curtius rearrangement, and reductive methylation, with starting materials such as methyl trans-cinnamates and ethyl diazoacetate.
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