Next Article in Journal
A Novel Disulfide-Containing Polycationic Amphiphile: 1,28-Di[(cholest-5-en-3β-yl)disulfanyl]-4,25-dioxo-3,8,12,17,21,26-hexaazaoctacosane Tetrahydrochloride
Next Article in Special Issue
Previous Article in Journal / Special Issue
Article Menu

Export Article

Open AccessCommunication
Molbank 2018, 2018(1), M980;

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

Institute of Organic and Medicinal Chemistry, Medical School, University of Pécs, Szigeti st. 12, H-7624 Pécs, Hungary
Institute of Pharmacognosy, University of Pécs, Rókus st. 2, H-7624 Pécs, Hungary
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)
Full-Text   |   PDF [703 KB, uploaded 1 February 2018]


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
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).

Supplementary materials


Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molbank EISSN 1422-8599 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top