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Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts
The reactivity of N -cyanomethyl quaternary salts of 4-, 5- and 7-azaindoles towards salicylic aldehydes has been studied. The interaction of azaindolium salts with salicylic aldehydes proceeds as a base-promoted domino reaction, giving the corresponding chromenoimidazopyrrolopyridines. In the case...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
© Georg Thieme Verlag
2017
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6193216/ http://dx.doi.org/10.1055/s-0036-1589496 |
| _version_ | 1783364040652750848 |
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| author | Voskressensky, Leonid G. Storozhenko, Olga A. Festa, Alexey A. Novikov, Roman A. Varlamov, Alexey V. |
| author_facet | Voskressensky, Leonid G. Storozhenko, Olga A. Festa, Alexey A. Novikov, Roman A. Varlamov, Alexey V. |
| author_sort | Voskressensky, Leonid G. |
| collection | PubMed |
| description | The reactivity of N -cyanomethyl quaternary salts of 4-, 5- and 7-azaindoles towards salicylic aldehydes has been studied. The interaction of azaindolium salts with salicylic aldehydes proceeds as a base-promoted domino reaction, giving the corresponding chromenoimidazopyrrolopyridines. In the case of the 7-(cyanomethyl)-7-azaindolium salt, the reaction was found to be more sensitive, but the use of the 1-methyl-substituted salt allowed the synthesis of the desired compounds, incorporating the heterocyclic core of isogranulatimide C, a marine natural product. |
| format | Online Article Text |
| id | pubmed-6193216 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2017 |
| publisher | © Georg Thieme Verlag |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-61932162018-10-30 Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts Voskressensky, Leonid G. Storozhenko, Olga A. Festa, Alexey A. Novikov, Roman A. Varlamov, Alexey V. Synthesis (Stuttg) The reactivity of N -cyanomethyl quaternary salts of 4-, 5- and 7-azaindoles towards salicylic aldehydes has been studied. The interaction of azaindolium salts with salicylic aldehydes proceeds as a base-promoted domino reaction, giving the corresponding chromenoimidazopyrrolopyridines. In the case of the 7-(cyanomethyl)-7-azaindolium salt, the reaction was found to be more sensitive, but the use of the 1-methyl-substituted salt allowed the synthesis of the desired compounds, incorporating the heterocyclic core of isogranulatimide C, a marine natural product. © Georg Thieme Verlag 2017-06-19 2017-04-04 /pmc/articles/PMC6193216/ http://dx.doi.org/10.1055/s-0036-1589496 Text en https://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
| spellingShingle | Voskressensky, Leonid G. Storozhenko, Olga A. Festa, Alexey A. Novikov, Roman A. Varlamov, Alexey V. Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts |
| title | Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts |
| title_full | Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts |
| title_fullStr | Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts |
| title_full_unstemmed | Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts |
| title_short | Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts |
| title_sort | synthesis of chromenoimidazoles, annulated with an azaindole moiety, through a base-promoted domino reaction of cyanomethyl quaternary salts |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6193216/ http://dx.doi.org/10.1055/s-0036-1589496 |
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