Issue 10, 2021
From the journal:

Organic Chemistry Frontiers

Copper-catalyzed aerobic oxidative domino cyclization of methyl azaarenes with 6-amino-pyrimidine-2,4-diones and pyrazol-5-amines: access to dipyrimidine/dipyrazolo-fused pyridines†

Rong-Ji Xie,‡a   Jun-Hua Liu,‡a   Qiu-Yi Zhang,‡a   Yi-Jie Yang,‡a   Li-Qun Song,a   Tian-Qi Shao,a   Kai-Xuan Liua  and  Yan-Ping Zhu ORCID logo *a  

* Corresponding authors

a School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, Shandong, P. R. China
E-mail: chemzyp@foxmail.com, chemzyp@ytu.edu.cn

Abstract

An aerobic copper-catalyzed oxidative domino cyclization of methyl azaarenes with 6-amino-pyrimidine-2,4-diones and pyrazol-5-amines has been developed, which enables access to dipyrimidine/dipyrazolo-fused pyridines. Cu(OTf)2 is used as a transition-metal catalyst. The oxidative annulation procedure exhibits excellent catalytic efficiency, high functional group compatibility and broad substrate scope, such as methyl quinolines, 2-methyl quinoxaline, 2-methyl benzo[f]quinoline, 2-methyl benzothiazole, 2-methyl benzoxazole and methyl pyridines.

Graphical abstract: Copper-catalyzed aerobic oxidative domino cyclization of methyl azaarenes with 6-amino-pyrimidine-2,4-diones and pyrazol-5-amines: access to dipyrimidine/dipyrazolo-fused pyridines

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Article information

DOI
https://doi.org/10.1039/D0QO01588A
Article type
Research Article
Submitted
17 Dec 2020
Accepted
11 Mar 2021
First published
15 Mar 2021

Org. Chem. Front., 2021,8, 2274-2279

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Copper-catalyzed aerobic oxidative domino cyclization of methyl azaarenes with 6-amino-pyrimidine-2,4-diones and pyrazol-5-amines: access to dipyrimidine/dipyrazolo-fused pyridines

R. Xie, J. Liu, Q. Zhang, Y. Yang, L. Song, T. Shao, K. Liu and Y. Zhu, Org. Chem. Front., 2021, 8, 2274 DOI: 10.1039/D0QO01588A

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