Synthesis of Aminofuropyridines via the Reaction of Aminosilanes with Pyridoxal

摘要

Synthesis of functionalized derivatives of pyridoxal (vitamin B6) and their biological activity are currently an active area of investigation [1-3]. We studied a possibility of modifying pyridoxal using aminosilanes and silazanes. The reactions of aliphatic and aromatic aldehydes with aminosilanes and silylamides of carboxylic acids occurred via attachment of the carbonyl reagent at the Si-N bond to form the corresponding trimethylsiloxy derivatives. In these reactions zinc chloride, lithium perchlorate, p-toluenesulfonic acid, and trimethylsilyl triflate were used as catalysts [4-9]. Depending on the reaction conditions, the interaction of aminosilanes with α,β-unsaturated aldehydes resulted in 1,3-bis(dialkyl-amino)alkenes or the corresponding aminals [10, 11].