CC BY-ND-NC 4.0 · SynOpen 2019; 03(04): 108-113
DOI: 10.1055/s-0039-1690222
paper
Copyright with the author(s) (2019) The author(s)

Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers

Vladimír Dacho
a  Department of Organic Chemistry, Slovak University of Technology in Bratislava, Radlinského 9, SK-81237 Bratislava, Slovakia   Email: peter.szolcsanyi@stuba.sk
,
Dária Nitrayová
a  Department of Organic Chemistry, Slovak University of Technology in Bratislava, Radlinského 9, SK-81237 Bratislava, Slovakia   Email: peter.szolcsanyi@stuba.sk
,
Michal Šoral
b  Central Laboratories, Slovak University of Technology in Bratislava, Radlinského 9, SK-81237 Bratislava, Slovakia
,
Andrea Machyňáková
c  Department of Analytical Chemistry, Slovak University of Technology in Bratislava, Radlinského 9, SK-81237 Bratislava, Slovakia
,
Ján Moncoľ
d  Department of Inorganic Chemistry, Slovak University of Technology in Bratislava, Radlinského 9, SK-81237 Bratislava, Slovakia
,
a  Department of Organic Chemistry, Slovak University of Technology in Bratislava, Radlinského 9, SK-81237 Bratislava, Slovakia   Email: peter.szolcsanyi@stuba.sk
› Author Affiliations
This work was supported by the Science and Technology Assistance Agency (Agentúra na Podporu Výskumu a Vývoja, contract No. APVV-15-0355). This article was created with the support of the MŠVVaŠ of the Slovak Republic within the Research and Development Operational Programme for the project ‘University Science Park of STU Bratislava’ (IMTS project No. 26240220084) co-funded by the European Regional Development Fund.
Further Information

Publication History

Received: 27 August 2019

Accepted after revision: 07 October 2019

Publication Date:
21 October 2019 (online)

Abstract

The reaction of tosylated 2-alkoxypyrazines with potassium halides led to the unexpected formation of N-alkylated pyrazinones. Such rare example of substitutive C–O → C–N rearrangement on pyrazines was then scrutinised by using various nucleophiles to afford the respective products in moderate to good yields. This method provides a direct access to N-alkylated-1H-pyrazin-2-ones. The formation of the rearranged products is conveniently and reliably determined by characteristic NMR shifts of their heteroaromatic protons.

Supporting Information

 
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