Title

Five- and Six-Membered Ring Opening of Pyroglutamic Diketopiperazine

Document Type

Article

Publication Date

3-22-2002

Department

Polymers and High Performance Materials

Abstract

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.

Publication Title

Journal of Organic Chemistry

Volume

67

Issue

6

First Page

1820

Last Page

1826