Tetrahedron letters

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

DJ Hartley, B Iddon

Index: Hartley, David J.; Iddon, Brian Tetrahedron Letters, 1997 , vol. 38, # 26 p. 4647 - 4650

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Citation Number: 22

Abstract

2, 4, 5-Tribromo-1-vinylimidazole was prepared from 2, 4, 5-tribromoimidazole and 1, 2- dibromoethane and its Br-atoms were replaced regioselectively 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 first synthesis of thieno [ ...