2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES
2-Aza-1,3-dienes bearing an activating trialkylsilyloxy group at C-3 have been prepared via three routes. The first route involves the silylation of N-acylimidates which are readily available from iminoether hydrochlorides and acid chlorides. According to a more general route towards these doubly ac...
| Main Authors: | , , , , , , , , |
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| Format: | Journal article |
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2012
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| _version_ | 1826265876796538880 |
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| author | Ghosez, L Bayard, P Nshimyumukiza, P Gouverneur, V Sainte, F Sainte, F Beaudegnies, R Beaudegnies, R Rivera, H Rivera, H Frisquehesbain, A Frisquehesbain, A Wynants, C Wynants, C |
| author_facet | Ghosez, L Bayard, P Nshimyumukiza, P Gouverneur, V Sainte, F Sainte, F Beaudegnies, R Beaudegnies, R Rivera, H Rivera, H Frisquehesbain, A Frisquehesbain, A Wynants, C Wynants, C |
| author_sort | Ghosez, L |
| collection | OXFORD |
| description | 2-Aza-1,3-dienes bearing an activating trialkylsilyloxy group at C-3 have been prepared via three routes. The first route involves the silylation of N-acylimidates which are readily available from iminoether hydrochlorides and acid chlorides. According to a more general route towards these doubly activated dienes, N-trialkylsilylimidates and N-trialkylsilylimines derived from non-enolizable aldehydes were conveniently converted in a one-pot sequence into the corresponding azadienes by reaction with an acid chloride in the presence of triethylamine. Finally, cyclic dienes could be prepared by direct silylation of glutarimide on both oxygens with trialkylsilyltriflate in the presence of triethylamine. The configuration and conformation of 2-azadienes have been established by 1H, 13C and 15N NMR spectroscopy. © 1995 Elsevier Science Ltd. |
| first_indexed | 2024-03-06T20:30:29Z |
| format | Journal article |
| id | oxford-uuid:30ddf79e-34d7-4334-aa82-0f67f12a4007 |
| institution | University of Oxford |
| last_indexed | 2024-03-06T20:30:29Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:30ddf79e-34d7-4334-aa82-0f67f12a40072022-03-26T13:04:16Z2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIESJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:30ddf79e-34d7-4334-aa82-0f67f12a4007Symplectic Elements at Oxford2012Ghosez, LBayard, PNshimyumukiza, PGouverneur, VSainte, FSainte, FBeaudegnies, RBeaudegnies, RRivera, HRivera, HFrisquehesbain, AFrisquehesbain, AWynants, CWynants, C2-Aza-1,3-dienes bearing an activating trialkylsilyloxy group at C-3 have been prepared via three routes. The first route involves the silylation of N-acylimidates which are readily available from iminoether hydrochlorides and acid chlorides. According to a more general route towards these doubly activated dienes, N-trialkylsilylimidates and N-trialkylsilylimines derived from non-enolizable aldehydes were conveniently converted in a one-pot sequence into the corresponding azadienes by reaction with an acid chloride in the presence of triethylamine. Finally, cyclic dienes could be prepared by direct silylation of glutarimide on both oxygens with trialkylsilyltriflate in the presence of triethylamine. The configuration and conformation of 2-azadienes have been established by 1H, 13C and 15N NMR spectroscopy. © 1995 Elsevier Science Ltd. |
| spellingShingle | Ghosez, L Bayard, P Nshimyumukiza, P Gouverneur, V Sainte, F Sainte, F Beaudegnies, R Beaudegnies, R Rivera, H Rivera, H Frisquehesbain, A Frisquehesbain, A Wynants, C Wynants, C 2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES |
| title | 2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES |
| title_full | 2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES |
| title_fullStr | 2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES |
| title_full_unstemmed | 2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES |
| title_short | 2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES |
| title_sort | 2 aza 1 3 dienes methods of synthesis and stereochemical studies |
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