Selenium-Containing Heterocycles from Isoselenocyanates: Synthesis of 5-Amino-2,4-dihydro-3H-1,2,4-triazole-3-selones

✍ Scribed by Geoffroy L. Sommen; Anthony Linden; Heinz Heimgartner

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: German
• Weight: 132 KB
• Volume: 90
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200790067

✦ Synopsis

Abstract

The reaction of S‐methylisothiosemicarbazide hydroiodide (=S‐methyl hydrazinecarboximidothioate hydroiodide; 1), prepared from thiosemicarbazide by treatment with MeI in EtOH, and aryl isoselenocyanates 5 in CH~2~Cl~2~ affords 3__H__‐1,2,4‐triazole‐3‐selone derivatives 7 in good yield (Scheme 2, Table 1). During attempted crystallization, these products undergo an oxidative dimerization to give the corresponding bis(4__H__‐1,2,4‐triazol‐3‐yl) diselenides 11 (Scheme 3). The structure of 11a was established by X‐ray crystallography.