
TY  - JOUR
A1  - Laws, Melissa J. 
A1  - Schiesser, Carl H. 
A1  - White, Jonathan M. 
A1  - Zheng, Shi-Long 
T1  - 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).
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2000
VL  - 53
IS  - 4
SP  - 277
EP  - 283
KW  - Ab initio molecular orbital calculations; diselenide; selenium; synthesis; thiophen; X-ray crystal structure.
UR  - https://doi.org/10.1071/CH99127 
N2  - 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). 
ER  -

