
%0 Journal Article
%A Laws, Melissa J. 
%A Schiesser, Carl H. 
%A White, Jonathan M. 
%A Zheng, Shi-Long 
%T Novel Analogues of Ebselen-Preparation of 2-Alkylthieno[2,3<emph type="2">-d</emph>]isoselenazol-3(2<emph type="2">H</emph>)-ones by Peroxide-Mediated Ring-Closure of 3,3'-Diselenobis(<emph type="2">N</emph>-alkylthiophencarboxamides).
%J Australian Journal of Chemistry
%D 2000/07/21
%V 53
%N 4
%P 277-283
%K Ab initio molecular orbital calculations; diselenide; selenium; synthesis; thiophen; X-ray crystal structure.
%R https://doi.org/10.1071/CH99127
%U https://www.publish.csiro.au/paper/CH99127 
%X Studies toward the preparation of novel thiophen analogues of the anti-inflammatory compound Ebselen are presented. We report that treatment of 3,3&#8242; -diselenobis(N-alkylthiophen-2-carboxamides) (13; R = Me, Pri, But, Ph) with benzoyl peroxide in benzene under reflux affords the corresponding 2-alkylthieno&#91;2,3-d&#93;isoselenazol-3(2H)-ones (7) in 10&#8211;73% yield, except for the phenyl derivative (13; R = Ph) which proved too insoluble to react. Irradiation of the PTOC imidate esters of 2-benzylseleno-N-butylthiophen-3-carboxamide (9) and 3-benzylseleno-N-butylthiophen-2-carboxamide (12) provides none of the expected Ebselen analogues. This failure to ring-close is discussed in terms of conformational rigidity in amidyl radicals (22) and (23). 
