Regioselectivity Amination of Usnic Acid by Ammonia in Water
Usnic acid is a well-known secondary lichen metabolite exhibiting a broad spectrum of biological activity. Previously it was shown that the reaction of usnic acid with various amines resulted in enamine-bond formation instead of the C(11)=O carbonyl group. Enamines obtained have a pronounced biologi...
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MDPI AG
2023-04-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/2/M1618 |
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| author | Aleksandr Filimonov Olga Luzina Yuri Gatilov Nariman Salakhutdinov |
| author_facet | Aleksandr Filimonov Olga Luzina Yuri Gatilov Nariman Salakhutdinov |
| author_sort | Aleksandr Filimonov |
| collection | DOAJ |
| description | Usnic acid is a well-known secondary lichen metabolite exhibiting a broad spectrum of biological activity. Previously it was shown that the reaction of usnic acid with various amines resulted in enamine-bond formation instead of the C(11)=O carbonyl group. Enamines obtained have a pronounced biological activity. In this work, we have shown that the reaction of usnic acid with ammonia can be regioselective if the solvent is replaced by water. The regioselectivity of that reaction depends on temperature and ammonia quantity. The C-1 enamine as only product formation has been obtained by the usnic acid reaction with an excess of ammonia (20 eq.) in water with cooling (+9 °C). |
| first_indexed | 2024-03-11T02:07:38Z |
| format | Article |
| id | doaj.art-b525048e92404e7da05a99e42a8e9064 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T02:07:38Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-b525048e92404e7da05a99e42a8e90642023-11-18T11:46:38ZengMDPI AGMolbank1422-85992023-04-0120232M161810.3390/M1618Regioselectivity Amination of Usnic Acid by Ammonia in WaterAleksandr Filimonov0Olga Luzina1Yuri Gatilov2Nariman Salakhutdinov3N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9, Akademika Lavrentieva Ave., 630090 Novosibirsk, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9, Akademika Lavrentieva Ave., 630090 Novosibirsk, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9, Akademika Lavrentieva Ave., 630090 Novosibirsk, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9, Akademika Lavrentieva Ave., 630090 Novosibirsk, RussiaUsnic acid is a well-known secondary lichen metabolite exhibiting a broad spectrum of biological activity. Previously it was shown that the reaction of usnic acid with various amines resulted in enamine-bond formation instead of the C(11)=O carbonyl group. Enamines obtained have a pronounced biological activity. In this work, we have shown that the reaction of usnic acid with ammonia can be regioselective if the solvent is replaced by water. The regioselectivity of that reaction depends on temperature and ammonia quantity. The C-1 enamine as only product formation has been obtained by the usnic acid reaction with an excess of ammonia (20 eq.) in water with cooling (+9 °C).https://www.mdpi.com/1422-8599/2023/2/M1618usnic acidaminationusnic acid enamine |
| spellingShingle | Aleksandr Filimonov Olga Luzina Yuri Gatilov Nariman Salakhutdinov Regioselectivity Amination of Usnic Acid by Ammonia in Water Molbank usnic acid amination usnic acid enamine |
| title | Regioselectivity Amination of Usnic Acid by Ammonia in Water |
| title_full | Regioselectivity Amination of Usnic Acid by Ammonia in Water |
| title_fullStr | Regioselectivity Amination of Usnic Acid by Ammonia in Water |
| title_full_unstemmed | Regioselectivity Amination of Usnic Acid by Ammonia in Water |
| title_short | Regioselectivity Amination of Usnic Acid by Ammonia in Water |
| title_sort | regioselectivity amination of usnic acid by ammonia in water |
| topic | usnic acid amination usnic acid enamine |
| url | https://www.mdpi.com/1422-8599/2023/2/M1618 |
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