Issue 17, 2020
From the journal:

RSC Advances

Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines†

Stanislav S. Shcherbakov,*a   Artyom Yu. Magometov,a   Viktoriia Yu. Shcherbakova,a   Alexander V. Aksenov, ORCID logo a   Dmitriy A. Domenyuk,b   Vladimir A. Zelenskyb  and  Michael Rubin ORCID logo *ac  

* Corresponding authors

a Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation
E-mail: alexaks05@rambler.ru

b Department of General Practice Dentistry and Child Dentistry, Stavropol State Medical University, 310 Mira Street, Stavropol 355017, Russian Federation

c Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, KS 66045-7582, USA
E-mail: mrubin@ku.edu
Tel: +1-785-864-5071

Abstract

A new synthetic protocol for preparation of medicinally important 4-aryl-5-alkynylpyrimidines is described. The featured approach involves a sequence of chemo- and regioselective Brønsted acid-catalyzed electrophilic alkylation of arenes with 5-bromopyrimidine, followed by oxidative re-aromatization of the formed dihydropyrimidine ring. Finally, palladium-catalyzed Sonogashira cross-coupling reaction provided an end-game strategy.

Graphical abstract: Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines

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Article information

DOI
https://doi.org/10.1039/D0RA01335H
Article type
Paper
Submitted
11 Feb 2020
Accepted
05 Mar 2020
First published
10 Mar 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 10315-10321

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Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines

S. S. Shcherbakov, A. Yu. Magometov, V. Yu. Shcherbakova, A. V. Aksenov, D. A. Domenyuk, V. A. Zelensky and M. Rubin, RSC Adv., 2020, 10, 10315 DOI: 10.1039/D0RA01335H

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