CONTRIBUTION TO THE KNOWLEDGE OF Γ-Aminocrotonic ACID. VINYLOGS OF Α-Amino ACIDS. I

Abstract

It is possible that the vinylogs of -amino acids of the formula I, according to the principle of vinylogy (1), could prove to be interesting compounds, inter alia, as substrates for certain enzymes.

Synthesis and preliminary biological screening of certain 5-aralkyl pyrrolidine-3-carboxylic acids as anticonvulsants

“…These compounds bear the pyrrolidine-3-carboxylic acid ring structure which may be considered as a rigid cyclized form of γ-aminobutyric acid (GABA), which acts as an important inhibitory neurotransmitter in the central nervous system. Similar ring system is also found in the anticonvulsants gamibetal [19], gabapentin [20] and baclofen [21] (Figure 1). …”

1,3-Dipolar cycloadditions of 3,5-dichloro-2,4,6-trimethylbenzonitrile oxide to phenoxy-substituted allenes

“…10% of the starting nitrile oxide. 7 The product structures are consistent with elemental analyses and NMR, IR, and mass spectral data; both and 13C NMR spectra are available for diadduct 5 (see Experimental Section). Diadduct 7 was also obtained in an independent manner, i.e., by reacting 1 with 2-phenoxy-1,3-butadiene (8).…”

“…The mass spectrum of 6a shows intense peaks at m/e 332 (100%) and 43 (85%) due to the loss of the acetyl fragment from the molecular ion. In the light of the well-studied mass-spectral properties of substituted isoxazoles,8"12 this (7) The full characterization and identification of these side products was not performed, but their NMR spectra significantly showed signals only in the region 5 1.8-2.8.…”

Syntheses Of Alkylated Alkanedioic Acids

“…The acylation of diazoalkanes by acyl chlorides (41), however, has found some application in the preparation of alkylated dicarboxylic acids. While the simplest diazoalkane, diazomethane (155, 482, 483, 678), effects only an extension of the carbon chain, the use of diazoethane (49) introduces also a methyl branch. Should this reaction prove to be capable of extension to other higher diazoalkanes, it would provide an effective general method for the synthesis of «-alkylated dicarboxylic acids.…”