Borane adducts of punicine and of its dehydroxy derivatives (pyridinium-1-yl)-2- and 3-phenolates
| Autor: | Eike G. Hübner, Colin Herzberger, Felix Lederle, Martin Nieger, Christian F. Otto, Tyll Freese, Ming Liu, Andreas Schmidt, Jan C. Namyslo |
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| Přispěvatelé: | Department of Chemistry |
| Rok vydání: | 2020 |
| Předmět: |
Tris
116 Chemical sciences DIPOLAR Mesomeric betaine Conjugated system Borane 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Cross-conjugation Adduct ACTIVATION chemistry.chemical_compound Betaine Pyridinium-phenolate N-HETEROCYCLIC CARBENES Drug Discovery 4-AMINOQUINOLINES Picoline FRUSTRATED LEWIS PAIR Conjugation 010405 organic chemistry Organic Chemistry REARRANGEMENTS PYRAZOLE Tautomer BORON ADDUCTS 0104 chemical sciences Tris(pentafluorophenyl)borane chemistry MESOMERIC BETAINES COMPLEXES Pyridinium |
| Zdroj: | Tetrahedron. 76:131627 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2020.131627 |
| Popis: | The natural product punicine (Punica granatum) exists in two tautomeric forms, the cross-conjugated mesomeric betaine 1-(pyridinium-1-yl)-2-hydroxy-phenyl-5-olate and the conjugated mesomeric betaine 1-(pyridinium-1-yl)-5-hydroxy-phenyl-2-olate. Punicine as well as its picoline derivatives reacted with tris(pentafluorophenyl)borane exclusively at the 2'-olate group to form zwitterionic borates. Correspondingly, the 5'-dehydroxy derivate of punicine, the conjugated heterocyclic mesomeric betaine 1-(pyridinium-1-yl)-phenyl-2-olate and its picoline derivatives also gave borates, whereas analogous reactions of the cross-conjugated isomer 2'-dehydroxypunicine [1-(pyridinium-1-yl)-phenyl-3-olatel did not result in the formation of stable adducts. (C) 2020 Elsevier Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
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