Facile conversion of Biginelli 3,4-dihydropyrimidin-2(1H)-thiones to 2-(2-hydroxy-2-arylvinyl) dihydropyrimidines via Eschenmoser coupling |
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| Authors: | Sukhdeep Singh Michael Gebinoga |
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| Affiliation: | a MacroNano®, Junior Research Group Microfluidics and Biosensors, Technische Universität Ilmenau, Institute for Micro and Nanotechnologies, Gustav-Kirchhoff Str. 5, 98693 Ilmenau, Germany
b Department of Physical Chemistry and Microreaction Technology, Technische Universität Ilmenau, Institute for Micro and Nanotechnologies, Gustav-Kirchhoff Str. 5, 98693 Ilmenau, Germany |
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| Abstract: | A one-pot, two-step synthesis protocol for the conversion of Biginelli 3,4-dihydropyrimidin-2(1H)-thiones to 2-(2-hydroxy-2-arylvinyl) dihydropyrimidine (DHPM) derivatives via Eschenmoser sulfide contraction coupling is described. Solution phase as well as solid-supported protocol was carried out for the decoration of the Biginelli DHMP scaffold at the C-2 position. The scope of the optimized protocol is demonstrated for different DHMP precursors. |
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| Keywords: | Eschenmoser Sulfide contraction Eschenmoser coupling Polymer supported Triphenylphosphine DHPM Biginelli Privileged structure Drug research |
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