A Dieckmann cyclization route to piperazine-2,5-diones

J Org Chem. 2012 Jun 1;77(11):5125-31. doi: 10.1021/jo3007144. Epub 2012 May 14.

Abstract

Piperazine-2,5-diones are formed by Dieckmann cyclization (NaH, THF) of substructures of the type CH(2)-N(R)C(O)CH(2)N(R')CO(2)Ph in which the terminal methylene (CH(2)) that is adjacent to nitrogen closes onto the carbonyl group of the phenyl carbamate unit at the other end of the chain. R and R' are alkyl groups, and the terminal methylene is activated by a ketone carbonyl, a nitrile, an ester, or a phosphoryl group. The starting materials are assembled by standard acylation and oxidation processes, starting from a β-(alkylamino)alcohol, an (alkylamino)acetonitrile, an (alkylamino) ester, or an (alkylamino)methyl phosphonate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nitriles / chemistry*
  • Organophosphonates / chemistry*
  • Piperazine
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry*

Substances

  • Nitriles
  • Organophosphonates
  • Piperazines
  • Piperazine