Synlett 2014; 25(15): 2189-2195
DOI: 10.1055/s-0034-1378525
letter
© Georg Thieme Verlag Stuttgart · New York

A Synthetic and Structural Study of Arylselenoamides and 2,4-Diaryl-1,3- Selenazoles

Guoxiong Hua
EaStCHEM School of Chemistry, University of St Andrews, Fife, KY16 9ST, UK   Fax: +44(1334)463384   Email: jdw3@st-and.ac.uk
,
Junyi Du
EaStCHEM School of Chemistry, University of St Andrews, Fife, KY16 9ST, UK   Fax: +44(1334)463384   Email: jdw3@st-and.ac.uk
,
Alexandra M. Z. Slawin
EaStCHEM School of Chemistry, University of St Andrews, Fife, KY16 9ST, UK   Fax: +44(1334)463384   Email: jdw3@st-and.ac.uk
,
J. Derek Woollins*
EaStCHEM School of Chemistry, University of St Andrews, Fife, KY16 9ST, UK   Fax: +44(1334)463384   Email: jdw3@st-and.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 30 April 2014

Accepted after revision: 20 June 2014

Publication Date:
28 July 2014 (online)


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.

Supporting Information