Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers
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 moder...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Georg Thieme Verlag KG
2019-10-01
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| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690222 |
| _version_ | 1818330449236197376 |
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| author | Vladimír Dacho Dária Nitrayová Michal Šoral Andrea Machyňáková Ján Moncoľ Peter Szolcsányi |
| author_facet | Vladimír Dacho Dária Nitrayová Michal Šoral Andrea Machyňáková Ján Moncoľ Peter Szolcsányi |
| author_sort | Vladimír Dacho |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-13T13:04:08Z |
| format | Article |
| id | doaj.art-1ab48133fcd44259bb2031f8a1bc4c04 |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-12-13T13:04:08Z |
| publishDate | 2019-10-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-1ab48133fcd44259bb2031f8a1bc4c042022-12-21T23:44:53ZengGeorg Thieme Verlag KGSynOpen2509-93962019-10-01030410811310.1055/s-0039-1690222Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl EthersVladimír Dacho0Dária Nitrayová1Michal Šoral2Andrea Machyňáková3Ján Moncoľ4Peter Szolcsányi5Department of Organic Chemistry, Slovak University of Technology in BratislavaDepartment of Organic Chemistry, Slovak University of Technology in BratislavaCentral Laboratories, Slovak University of Technology in BratislavaDepartment of Analytical Chemistry, Slovak University of Technology in BratislavaDepartment of Inorganic Chemistry, Slovak University of Technology in BratislavaDepartment of Organic Chemistry, Slovak University of Technology in BratislavaAbstract 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.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690222pyrazinonesrearrangementsn reactionnmr spectroscopyx-ray crystal structure analysis |
| spellingShingle | Vladimír Dacho Dária Nitrayová Michal Šoral Andrea Machyňáková Ján Moncoľ Peter Szolcsányi Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers SynOpen pyrazinones rearrangement sn reaction nmr spectroscopy x-ray crystal structure analysis |
| title | Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers |
| title_full | Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers |
| title_fullStr | Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers |
| title_full_unstemmed | Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers |
| title_short | Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers |
| title_sort | access to n alkylpyrazin 2 ones via c o to c n rearrangement of pyrazinyl ethers |
| topic | pyrazinones rearrangement sn reaction nmr spectroscopy x-ray crystal structure analysis |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690222 |
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