Synthesis and conformational behaviour of tri-3-methyltrianthranilides. A new example of spontaneous resolution and inclusion compound formation on crystallisation

Simon J. Edge*, W. David Ollis, Julia Stephanidou Stephanatou, J. Eraser Stoddart, David J. Williams, Kwamena A. Woode

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The tri-3-methyltrianthranilide derivatives (7)-(9) have been synthesised. Dynamic 1H n.m.r. spectroscopy indicates that the N,N′,N″-trimethyl derivative (8) exists in solution as slowly ring inverting (16 ⇌ 16*) enantiomeric helical conformations. X-Ray crystallography shows that the N,N′-dimethyl-N″-benzyl derivative (9) undergoes spontaneous resolution when it crystallises as a 1:1 adduct from toluene. The host molecules adopt a helical conformation (Figure 1) within a lattice structure that contains chiral channels (Figure 2) occupied by guest solvent molecules.

Original languageEnglish (US)
Pages (from-to)2229-2232
Number of pages4
JournalTetrahedron Letters
Volume22
Issue number23
DOIs
StatePublished - 1981

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and conformational behaviour of tri-3-methyltrianthranilides. A new example of spontaneous resolution and inclusion compound formation on crystallisation'. Together they form a unique fingerprint.

Cite this