Synthesis of bis-acyclonucleoside analogues bearing benzothienyl-1,2,4-Triazol-3-Yl-disulfide under conventional and microwave methods.
The oxidation of 5-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole-3-thiol (1) with a solution of iodine and potassium iodide at room temperature afforded [5-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole-3-yl]disulfide (2). In contrast, when the reaction mixture was heated or irradiated by MW, an unexpected additional product was obtained and identified as 3-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole (3); the ratio of products was 3:1. The preferred conformer of 2 was deduced from the theoretical calculation. The alkylation of compounds 2 and 3 with epichlorohydrin and hydroxyalkylating agents gave the corresponding N,N-bis- and N-acyclonucleosides analogues 8-15.
Department of Chemistry, Taibah University, Madinah, Saudi Arabia. aouadmohamedreda@yahoo.fr
Mohamed R
MR
Aouad
Nadjet
N
Rezki
Mouslim
M
Messali
El Sayed H
el SH
El Ashry
D000478:Alkylation; D002254:Carbonates / Q000737:chemistry; D004126:Dimethylformamide / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D008872:Microwaves; D008958:Models, Molecular; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011188:Potassium / Q000737:chemistry; D011193:Potassium Iodide / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
D002254:Carbonates; D009705:Nucleosides; D012997:Solvents; D011193:Potassium Iodide; D004126:Dimethylformamide; D007455:Iodine; C037593:potassium carbonate; D011188:Potassium