56805-18-6Relevant articles and documents
The Forgotten Pyrazines: Exploring the Dakin–West Reaction
Würdemann, Martien A.,Ni?u, Cristina,De Wildeman, Stefaan M. A.,Bernaerts, Katrien V.,Orru, Romano V. A.
, p. 8090 - 8100 (2020/06/09)
Pyrazines are an underreported class of N-heterocycles available from nitrogen-rich biomass presenting an interesting functional alternative for current aromatics. In this work, access to pyrazines obtained from amino acids by using the 90 year old Dakin–West reaction was explored. After a qualitative screening several functional proteinogenic amino acids proved good substrates for this reaction, which were successfully scaled to multigram scale synthesis of the corresponding intermediate α-acetamido ketones. Subsequently, the conditions towards pyrazine formation using δ-amino-levulinic acid were optimized, and these were employed to synthesize a relevant set of five functional dimethylpyrazines in high purity. These pyrazines can be considered a versatile toolbox of aromatic building blocks for a wide range of applications, such as in the synthesis of polymers or metal–organic frameworks.
SYNTHESIS OF 2-OXA AND 2-AZA ANALOGS OF PYRROLIZIDINE-3,5-DIONES (LUKES-SORM DILACTAM)
Nagasaka, Tatsuo,Hakamada, Rie,Kunii, Shin-ichi,Hamaguchi, Fumiko
, p. 619 - 630 (2007/10/02)
The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported.Optically active (+)-2-oxa and (+)-2-aza analogs and racemic 2-aza analog and its 1-methoxycarbonyl derivatives were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.
A Convenient Preparation of N-Acylpyroglutamic Acid
Imaki, Katsuhiro,Niwa, Haruki,Sakuyama, Shigeru,Okada, Takanori,Toda, Masaaki,Hayashi, Masaki
, p. 2699 - 2701 (2007/10/02)
Pyroglutamic acid reacted with acyl chloride in the presence of triethylamine in acetonitrile, yielding N-acylpyroglutamic acid without epimerization by way of mixed anhydride formation followed by intramolecular N-acylation.Keywords - angiotensin-converting enzyme; pyroglutamic acid; N-acylpyroglutamic acid; (2S)-1-pyroglutamic acid; N-acetyl-L-pyroglutamic acid