N-(2-tetrahydrofuranyl)azole nucleoside analogs by reactions of azoles with dihalomethanes in tetrahydrofuran

✍ Scribed by Jerzy Zadykowicz; Pierre G. Potvin

• Book ID: 102341325
• Publisher: Journal of Heterocyclic Chemistry
• Year: 1999
• Tongue: English
• Weight: 353 KB
• Volume: 36
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570360308

✦ Synopsis

Abstract

The reactions of the mono‐N‐substituted bispyrazolylpyridine 2‐(1‐methyl‐4,5,6,7‐tetxahydroindazol‐3‐yl)‐6‐(2__H__‐4,5,6,7‐tetrahydroindazol‐3‐yl)pyridine, 3,5‐dimethylpyrazole and benzimidazole with sodium hydride and diiodomethane or dibromomethane in tetrahydrofuran produced the unexpected N‐tetrahydrofuran‐2‐yl adducts as well as the expected diazolylmethanes. These side‐reactions are thought to involve the 2‐halo tetrahydrofuran derivative resulting from a free‐radical halogenation by the dihalomethane.