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Open AccessCommunication

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.
Molbank 2018, 2018(1), M980; https://doi.org/10.3390/M980
Received: 19 December 2017 / Revised: 30 January 2018 / Accepted: 31 January 2018 / Published: 1 February 2018
(This article belongs to the Special Issue Heterocycles)
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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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. https://doi.org/10.3390/M980

AMA Style

Úr G, Gulyás Fekete G, Hideg K, Kálai T. N-Vinylation of Imidazole and Benzimidazole with a Paramagnetic Vinyl Bromide. Molbank. 2018; 2018(1):M980. https://doi.org/10.3390/M980

Chicago/Turabian Style

Úr, Györgyi; Gulyás Fekete, Gergely; Hideg, Kálmán; Kálai, Tamás. 2018. "N-Vinylation of Imidazole and Benzimidazole with a Paramagnetic Vinyl Bromide" Molbank 2018, no. 1: M980. https://doi.org/10.3390/M980

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