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Open AccessCommunication
Molbank 2018, 2018(1), M980; doi:10.3390/M980

N-Vinylation of Imidazole and Benzimidazole with a Paramagnetic Vinyl Bromide

1
Institute of Organic and Medicinal Chemistry, Medical School, University of Pécs, Szigeti st. 12, H-7624 Pécs, Hungary
2
Institute of Pharmacognosy, University of Pécs, Rókus st. 2, H-7624 Pécs, Hungary
3
Szentágothai Research Center, Ifjúság st. 20, H-7624 Pécs, Hungary
*
Author to whom correspondence should be addressed.
Received: 19 December 2017 / Revised: 30 January 2018 / Accepted: 31 January 2018 / Published: 1 February 2018
(This article belongs to the Special Issue Heterocycles)
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Abstract

An N-vinylation of imidazole and benzimidazole with a paramagnetic vinyl bromide was investigated. Among the tested procedures, Pd-catalyzed reaction was the most powerful one. The N-vinylation of 2-aminobenzimidazole with a β-bromo-α,β-unsaturated pyrroline nitroxide aldehyde offered 1,1,3,3-tetramethyl-1H-benzimidazo[1,2-a]pyrrolo[3,4-e]pyrimidin-2(3H)-yloxyl radical and the corresponding non-cyclized Schiff base. The reaction of a β-bromo-α,β-unsaturated pyrroline nitroxide aldehyde with imidazole gave β-imidazo-α,β-unsaturated pyrroline nitroxide aldehyde, which was reduced to the alcohol and converted to an unstable allyl chloride. View Full-Text
Keywords: imidazole; benzimidazole; nitroxide; cross coupling reactions imidazole; benzimidazole; nitroxide; cross coupling reactions
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Úr, G.; Gulyás Fekete, G.; Hideg, K.; Kálai, T. N-Vinylation of Imidazole and Benzimidazole with a Paramagnetic Vinyl Bromide. Molbank 2018, 2018, M980.

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