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Título: | Expedient one-pot synthesis of novel chiral 2-substituted 5-phenyl-1,4-benzodiazepine scaffolds from amino acid-derived amino nitriles |
Autor: | Herrero, Susana; García-López, M. Teresa CSIC ; Herranz, Rosario CSIC ORCID | Palabras clave: | Nitrogen compounds Peptides and proteins Post-translational modification Reaction products Redox reactions |
Fecha de publicación: | 2-may-2003 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 68(11): 4582-4585 (2003) | Resumen: | An efficient and stereocontrolled synthesis of phenylalanine- and tryptophan-derived 5-phenyl-1,4-benzodiazepines is described. This new methodology involves, as a key step, the synthesis of 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepines by a one-pot cyano reduction and reductive cyclization of the appropriate amino nitrile, which were obtained via a modified Strecker reaction of N-protected α-amino aldehydes with 2-aminobenzophenone and trimethylsilyl cyanide. The subsequent reduction of these 2,3-dihydro-1H-1,4-benzodiazepines, followed by regioselective alkylation or acylation at position 4, led to 2,4-disubstituted-5-phenyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine. | Versión del editor: | http://dx.doi.org/10.1021/jo034286c | URI: | http://hdl.handle.net/10261/336154 | DOI: | 10.1021/jo034286c | ISSN: | 0022-3263 | E-ISSN: | 1520-6904 |
Aparece en las colecciones: | (IQM) Artículos |
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accesoRestringido.pdf | 15,38 kB | Adobe PDF | Visualizar/Abrir |
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