A synthetic and structural study of arylselenoamides and 2,4-diaryl-1,3- selenazoles

Guoxiong Hua, Junyi Du, Alexandra M.Z. Slawin, J. Derek Woollins*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The systematic preparation of 2,4-diaryl-1,3-selenazoles was carried out by two-component cyclization of the primary selenoamides with α-halo ketones. Selenoamides were obtained from the reaction of Woollins' reagent with arylnitrile, followed by hydrolysis with water. Three selenoamides have close structural similarities along with intermolecular interactions such as the strong N-H···O hydrogen bonding, the weak N-H···Se, C-H···O/N/Se intermolecular interactions and π-π stacking interactions; meanwhile, the newly formed five-membered N-C-Se-C-C rings in ten 2,4-diaryl-1,3-selenazoles have either planar or near-planar conformations along with the weak C- H···O/N/Se/Br/Cl intermolecular interactions and π-π stacking interactions. In addition, the weak Se···Se close contacts in four cases and the C-H···N intramolecular interactions in two structures were also observed within the all solid structures.

Original languageEnglish
Article numberst-2014-b0355-l
Pages (from-to)2189-2195
Number of pages7
JournalSynlett
Volume25
Issue number15
DOIs
Publication statusPublished - 1 Jan 2014

Keywords

  • 1,3-selenazoles
  • selenoamides
  • Woollins' reagent
  • X-ray crystal structures
  • α-halo ketones

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