Synthesis of pseudopeptidic (S)-6-amino-5-oxo-1,4-diazepines and (S)-3-benzyl-2-oxo-1,4-benzodiazepines by an Ugi 4CC Staudinger/aza-Wittig sequence |
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Authors: | Paulina Lecinska Daniel Moreno Stefano Marcaccini |
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Institution: | a Department of Chemistry, Faculty of Science, Universidad de Burgos, 09001 Burgos, Spain b Department of Chemistry, Polo Scientifico, Università di Firenze, 50019 Sesto Fiorentino (FI), Italy |
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Abstract: | Sequential Ugi reaction between p-substituted arylglyoxals, alkylamines, cyclohexyl isocyanide and 3-azido-(S)-2-(tert-butoxycarbonylamino)propanoic acid, followed by a Staudinger/aza-Wittig cyclization in the presence of triphenylphosphine, gave rise to enantiomerically pure N-cyclohexyl 4-alkyl-2-aryl-5-oxo-(S)-6-(tert-butoxycarbonylamino)-4,5,6,7-tetrahydro-1H-1,4-diazepine-3-carboxamides, that can be useful for new drug design. By the same sequence, p-substituted benzaldehydes, 2-aminobenzophenone, cyclohexyl isocyanide and (S)-3-phenyl-2-azidopropionic acid gave rise to N-cyclohexyl 2-((S)-3-benzyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzoe]1,4]diazepin-1-yl)-(R/S)-2-arylacetamides. |
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Keywords: | Isocyanide Ugi reaction Staudinger/aza-Wittig Diazepine Benzodiazepine |
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