Reaction of condensed cyclohexane isoxazolones with Grignard rea gents
Synthesis of new 2-acyl derivatives of 1,3-cyclohexanediones, various variants of their subsequent chemical transformation are relevant for organic and bioorganic chemistry, since it is known that a large number of such substances are bioactive. The presence of several reaction centers in this serie...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | Belarusian |
| Published: |
Belarusian State University
2019-01-01
|
| Series: | Журнал Белорусского государственного университета: Химия |
| Subjects: | |
| Online Access: | https://journals.bsu.by/index.php/chemistry/article/view/1238 |
| _version_ | 1818924797672816640 |
|---|---|
| author | Наталья G. Vasilyeva Fjodor A. Lakhvich Alla L. Kozlova-Kozyrevskaya |
| author_facet | Наталья G. Vasilyeva Fjodor A. Lakhvich Alla L. Kozlova-Kozyrevskaya |
| author_sort | Наталья G. Vasilyeva |
| collection | DOAJ |
| description | Synthesis of new 2-acyl derivatives of 1,3-cyclohexanediones, various variants of their subsequent chemical transformation are relevant for organic and bioorganic chemistry, since it is known that a large number of such substances are bioactive. The presence of several reaction centers in this series of compounds makes it difficult to target specifically
the carbonyl group or other reaction centers in the reaction. To exclude the competitive course of adverse reactions in the targeted modification of the initial ones, the property of the β-diketone grouping is easily converted to isoxazoles, which are their latent form, which can easily be regenerated at certain stages of the synthetic process from the latter. Stability of the same isoxazole cycle under the conditions of many chemical reactions allows the directed effect on the cyclohexane fragment of molecules or make changes in the side acyl chain. To study the modification of 2-acylcyclohexane-1,3-diones on the cyclic part of the molecule, the Grignard reaction was studied using the cyclohexanoisoxazolones obtained earlier. However, it was not possible to isolate the expected products of 1,2-addition via the carbonyl group. Instead of them, compounds were isolated, to which the structure of alkylidenebenzo[d]isoxazoles was attributed. |
| first_indexed | 2024-12-20T02:31:02Z |
| format | Article |
| id | doaj.art-3099a0ff63ee478e84e57246e4d702e3 |
| institution | Directory Open Access Journal |
| issn | 2520-257X 2617-3980 |
| language | Belarusian |
| last_indexed | 2024-12-20T02:31:02Z |
| publishDate | 2019-01-01 |
| publisher | Belarusian State University |
| record_format | Article |
| series | Журнал Белорусского государственного университета: Химия |
| spelling | doaj.art-3099a0ff63ee478e84e57246e4d702e32022-12-21T19:56:33ZbelBelarusian State UniversityЖурнал Белорусского государственного университета: Химия2520-257X2617-39802019-01-01225291238Reaction of condensed cyclohexane isoxazolones with Grignard rea gentsНаталья G. Vasilyeva0Fjodor A. Lakhvich1Alla L. Kozlova-Kozyrevskaya2Belarusian State Pedagogical University named after Maxim Tank, 18 Savieckaja Street, Minsk 220030, BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 5/2 Kuprevicha Street, Minsk 220141, BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 5/2 Kuprevicha Street, Minsk 220141, BelarusSynthesis of new 2-acyl derivatives of 1,3-cyclohexanediones, various variants of their subsequent chemical transformation are relevant for organic and bioorganic chemistry, since it is known that a large number of such substances are bioactive. The presence of several reaction centers in this series of compounds makes it difficult to target specifically the carbonyl group or other reaction centers in the reaction. To exclude the competitive course of adverse reactions in the targeted modification of the initial ones, the property of the β-diketone grouping is easily converted to isoxazoles, which are their latent form, which can easily be regenerated at certain stages of the synthetic process from the latter. Stability of the same isoxazole cycle under the conditions of many chemical reactions allows the directed effect on the cyclohexane fragment of molecules or make changes in the side acyl chain. To study the modification of 2-acylcyclohexane-1,3-diones on the cyclic part of the molecule, the Grignard reaction was studied using the cyclohexanoisoxazolones obtained earlier. However, it was not possible to isolate the expected products of 1,2-addition via the carbonyl group. Instead of them, compounds were isolated, to which the structure of alkylidenebenzo[d]isoxazoles was attributed.https://journals.bsu.by/index.php/chemistry/article/view/12382-acylcyclohexane-1,3-dionessynthonscyclohexaneisoxazolonesgrignard reagentsnucleophilic addition |
| spellingShingle | Наталья G. Vasilyeva Fjodor A. Lakhvich Alla L. Kozlova-Kozyrevskaya Reaction of condensed cyclohexane isoxazolones with Grignard rea gents Журнал Белорусского государственного университета: Химия 2-acylcyclohexane-1,3-diones synthons cyclohexaneisoxazolones grignard reagents nucleophilic addition |
| title | Reaction of condensed cyclohexane isoxazolones with Grignard rea gents |
| title_full | Reaction of condensed cyclohexane isoxazolones with Grignard rea gents |
| title_fullStr | Reaction of condensed cyclohexane isoxazolones with Grignard rea gents |
| title_full_unstemmed | Reaction of condensed cyclohexane isoxazolones with Grignard rea gents |
| title_short | Reaction of condensed cyclohexane isoxazolones with Grignard rea gents |
| title_sort | reaction of condensed cyclohexane isoxazolones with grignard rea gents |
| topic | 2-acylcyclohexane-1,3-diones synthons cyclohexaneisoxazolones grignard reagents nucleophilic addition |
| url | https://journals.bsu.by/index.php/chemistry/article/view/1238 |
| work_keys_str_mv | AT natalʹâgvasilyeva reactionofcondensedcyclohexaneisoxazoloneswithgrignardreagents AT fjodoralakhvich reactionofcondensedcyclohexaneisoxazoloneswithgrignardreagents AT allalkozlovakozyrevskaya reactionofcondensedcyclohexaneisoxazoloneswithgrignardreagents |