Synthesis of fused tetrazole- and imidazole derivatives via iodocyclization

✍ Scribed by Fredrik Ek; Lars-Göran Wistrand; Torbjörn Frejd

• Book ID: 104205469
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 265 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)00818-4

✦ Synopsis

The possibility to prepare fused tetrazole-and imidazole derivatives by iodocyclization in moderate to excellent yields is demonstrated. In some examples the cyclizations were not following Baldwin's rules entirely, i.e. exo-selectivity. Nucleophilic substitution of the formed iodides gave different results depending on the hardness of the nucleophile. Thus, elimination of the iodide could be a problem but a substitution reaction with ethyl potassium xanthate and a radical reaction using acrylonitrile were tolerated. In addition, we showed that it is possible to selectively use three iodo substituents individually in one of the fused imidazole derivatives.