Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure
A convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.17.168 |
| _version_ | 1818724186958331904 |
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| author | Agnieszka Grajewska Maria Chrzanowska Wiktoria Adamska |
| author_facet | Agnieszka Grajewska Maria Chrzanowska Wiktoria Adamska |
| author_sort | Agnieszka Grajewska |
| collection | DOAJ |
| description | A convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted benzyl groups as the amine components followed by Pomeranz–Fritsch double cyclization reaction. By applying this method, several acids have been prepared in satisfactory yields. An unprecedented chemical behavior of a Petasis reaction product in diluted HCl solution leading to the formation of a phenylglycine derivative has been observed and the mechanism explaining such reactivity has been proposed. |
| first_indexed | 2024-12-17T21:22:25Z |
| format | Article |
| id | doaj.art-39567468088647bf812d42c957eab6b0 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T21:22:25Z |
| publishDate | 2021-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-39567468088647bf812d42c957eab6b02022-12-21T21:32:08ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-10-011712511251910.3762/bjoc.17.1681860-5397-17-168Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structureAgnieszka Grajewska0Maria Chrzanowska1Wiktoria Adamska2Faculty of Chemistry, Adam Mickiewicz University, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandFaculty of Chemistry, Adam Mickiewicz University, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandFaculty of Chemistry, Adam Mickiewicz University, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandA convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted benzyl groups as the amine components followed by Pomeranz–Fritsch double cyclization reaction. By applying this method, several acids have been prepared in satisfactory yields. An unprecedented chemical behavior of a Petasis reaction product in diluted HCl solution leading to the formation of a phenylglycine derivative has been observed and the mechanism explaining such reactivity has been proposed.https://doi.org/10.3762/bjoc.17.168amino acidscyclizationmulticomponent reactionssynthetic methodstetrahydroisoquinoline |
| spellingShingle | Agnieszka Grajewska Maria Chrzanowska Wiktoria Adamska Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure Beilstein Journal of Organic Chemistry amino acids cyclization multicomponent reactions synthetic methods tetrahydroisoquinoline |
| title | Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure |
| title_full | Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure |
| title_fullStr | Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure |
| title_full_unstemmed | Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure |
| title_short | Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure |
| title_sort | synthesis of new substituted 7 12 dihydro 6 12 methanodibenzo c f azocine 5 carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure |
| topic | amino acids cyclization multicomponent reactions synthetic methods tetrahydroisoquinoline |
| url | https://doi.org/10.3762/bjoc.17.168 |
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