Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media
Abstract Reaction of 3-formylchromone with cyclic secondary amines in methanol results in (E)-2-methoxy-3-(R2N-methylene)chroman-4-ones, while use of ethanol leads to (E)-2-morpholino-3-(morpholinomethylene)chroman-4-one or enaminoketones as dihydropyran ring-opening products. The solubility of the...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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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-0039-1690339 |
| _version_ | 1811335264849625088 |
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| author | Kirill S. Korzhenko Dmitry V. Osipov Vitaly A. Osyanin Yuri N. Klimochkin |
| author_facet | Kirill S. Korzhenko Dmitry V. Osipov Vitaly A. Osyanin Yuri N. Klimochkin |
| author_sort | Kirill S. Korzhenko |
| collection | DOAJ |
| description | Abstract
Reaction of 3-formylchromone with cyclic secondary amines in methanol results in (E)-2-methoxy-3-(R2N-methylene)chroman-4-ones, while use of ethanol leads to (E)-2-morpholino-3-(morpholinomethylene)chroman-4-one or enaminoketones as dihydropyran ring-opening products. The solubility of the formed products in alcoholic media is postulated to be a key factor that determines the reaction pathway. |
| first_indexed | 2024-04-13T17:21:39Z |
| format | Article |
| id | doaj.art-ad90589080864c56963f1b19d10d7f6b |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-04-13T17:21:39Z |
| publishDate | 2019-10-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-ad90589080864c56963f1b19d10d7f6b2022-12-22T02:37:58ZengGeorg Thieme Verlag KGSynOpen2509-93962019-10-01030416416810.1055/s-0039-1690339Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic MediaKirill S. KorzhenkoDmitry V. OsipovVitaly A. Osyanin0Yuri N. KlimochkinDepartment of Organic Chemistry, Samara State Technical UniversityAbstract Reaction of 3-formylchromone with cyclic secondary amines in methanol results in (E)-2-methoxy-3-(R2N-methylene)chroman-4-ones, while use of ethanol leads to (E)-2-morpholino-3-(morpholinomethylene)chroman-4-one or enaminoketones as dihydropyran ring-opening products. The solubility of the formed products in alcoholic media is postulated to be a key factor that determines the reaction pathway.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-16903393-formylchromone4-chromanonecyclic secondary aminesmichael reactionenamino ketones1h-azoles |
| spellingShingle | Kirill S. Korzhenko Dmitry V. Osipov Vitaly A. Osyanin Yuri N. Klimochkin Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media SynOpen 3-formylchromone 4-chromanone cyclic secondary amines michael reaction enamino ketones 1h-azoles |
| title | Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media |
| title_full | Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media |
| title_fullStr | Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media |
| title_full_unstemmed | Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media |
| title_short | Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media |
| title_sort | divergent pathways for reactions of 3 formylchromone with cyclic secondary amines in alcoholic media |
| topic | 3-formylchromone 4-chromanone cyclic secondary amines michael reaction enamino ketones 1h-azoles |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690339 |
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