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Use of the vinyl group as an efficient protecting group for azole N- atoms: Synthesis of polyfunctionalized imidazoles and thieno[2,3-d] ⇌ [3,2-d]imidazole

✍ Scribed by David J. Hartley; Brian Iddon

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 152 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00957-x

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✦ Synopsis

2,4,5-Tribromo-l-vinylimidazole was prepared from 2,4,5-tribromoimidazole and 1,2-dibromoethane and its Br-atoms were replaced regio~lectively in the order 2 --) 5 ---> 4 via Br --~ MgBr and other exchange reactions. Efficient removal of the vinyl groups from the resulting polyfunctionalized imidazoles was achieved with ozone or potassium permanganate. An extension of this methodology has allowed the flust synthesis of thieno[2,3-d] ~ [3,2-d]imidazole.

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