Protecting Group Free Synthesis of Carboxyl‐substituted Dihydropyrimidines Through Biginelli Reaction |
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| Authors: | Eugeniy N Ostapchuk Andrey S Plaskon Oleksandr O Grygorenko Andrey A Tolmachev Sergey V Ryabukhin |
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| Institution: | 1. Enamine Ltd., , Kyiv, 01103 Ukraine;2. Kyiv National Taras Shevchenko University, , Kyiv, 01033 Ukraine;3. The Institute of High Technologies, Kyiv National Taras Shevchenko University, , Kyiv, 03187 Ukraine |
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| Abstract: | Chlorotrimethylsilane‐promoted Biginelli‐type reaction of benzaldehyde, acetoacetic acid derivatives, and various carboxyl‐containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono‐substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one‐pot, protecting group free synthesis of dihydropyrimidines possessing carboxylic functionality. |
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| Keywords: | Biginelli reaction multicomponent reaction dihydropyrimidines ureas chlorotrimethylsilane |
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