Sequential Amino-Claisen Rearrangement/Intramolecular 1,3-Dipolar Cycloaddition/Reductive Cleavage Approach to the Stereoselective Synthesis of cis-4-Hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines
Abstract A novel stereoselective synthesis of CIS-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-ben...
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| Veröffentlicht in: | Synlett 2006-09, Vol.2006 (14), p.2275-2277 |
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| container_issue | 14 |
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| container_title | Synlett |
| container_volume | 2006 |
| creator | Gómez Ayala, Sandra Liliana Stashenko, Elena Palma, Alirio Bahsas, Alí Amaro-Luis, Juan Manuel |
| description | Abstract
A novel stereoselective synthesis of CIS-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-benzylanilines followed by amino-Claisen rearrangement, subsequent oxidation with in situ 1,3-dipolar cycloaddition affording isoxazolidines, and finally reductive cleavage of the isoxazolidinic N-O bond. |
| doi_str_mv | 10.1055/s-2006-949654 |
| format | Article |
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A novel stereoselective synthesis of CIS-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-benzylanilines followed by amino-Claisen rearrangement, subsequent oxidation with in situ 1,3-dipolar cycloaddition affording isoxazolidines, and finally reductive cleavage of the isoxazolidinic N-O bond.</abstract><doi>10.1055/s-2006-949654</doi><tpages>3</tpages></addata></record> |
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| subjects | letter |
| title | Sequential Amino-Claisen Rearrangement/Intramolecular 1,3-Dipolar Cycloaddition/Reductive Cleavage Approach to the Stereoselective Synthesis of cis-4-Hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines |
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