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Activation of hydrocinnamic acids with pentafluorophenol versus pentafluorothiophenol: Reactivity towards hexylamine |
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| Authors: | Fernanda MF Roleira Fernanda Borges José A Paixão Rui A Carvalho |
| Institution: | a CEF, Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, Coimbra University, 3000-295 Coimbra, Portugal b UQFM, Laboratory of Organic Chemistry, Faculty of Pharmacy, Porto University, 4050-047 Porto, Portugal c CEMDRX, Department of Physics, Faculty of Sciences and Technology, Coimbra University, 3004-516 Coimbra, Portugal d CNC, Department of Biochemistry, Faculty of Sciences and Technology, Coimbra University, 3004-516 Coimbra, Portugal |
| Abstract: | In this work we describe and compare the synthesis of four new hexylamides of hydrocinnamic acids, namely hexylamide of hydrocinnamic, 3,4-dimethoxyhydrocinnamic, 4-hydroxy-3-methoxyhydrocinnamic and 3,4-dihydroxyhydrocinnamic acids via pentafluorophenyl esters (PFPEs) versus pentafluorophenyl thioesters (PFPTs) intermediates. It was found that the PFPE are the best intermediates for this kind of synthesis giving reactions with less by products, easier work-up, higher overall yields and with the best reactivity towards hexylamine. The X-ray structures of two PFPE are also reported. |
| Keywords: | Hydrocinnamic acids Pentafluorophenyl esters Pentafluorophenyl thioesters Hexylamides Phenols X-ray structures |
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