Five- and Six-Membered Ring Opening of Pyroglutamic Diketopiperazine
Polymers and High Performance Materials
A variety of ring-opening reactions of pyroglutamic diketopiperazine at both the five-membered and six-membered rings is described. Mild, basic conditions facilitate nucleophilic attack by amines at the diketopiperazine carbonyls giving pyroglutamides in excellent yield. Reaction with nucleophiles under acidic conditions give bis-glutamate derivatives of 2,5-diketopiperazine (DKP). These reactions provide simple, two-step sequences to pyroglutamides and symmetrical diketopiperazines from commercial pyroglutamic acid with control of product dictated by reaction conditions, catalyst, and nucleophile.
Journal of Organic Chemistry
Parrish, D. A.,
Mathias, L. J.
(2002). Five- and Six-Membered Ring Opening of Pyroglutamic Diketopiperazine. Journal of Organic Chemistry, 67(6), 1820-1826.
Available at: http://aquila.usm.edu/fac_pubs/3649