Triacetic Acid Lactone (4-hydroxy-6-methyl-2-pyrone), or TAL is an organic compound that is very soluble and reactive in water. TAL is readily available from the fermentation of glucose. Its chemistry has not been studied as much as other pyrones such as, dehydroacetic acid, due to its high cost. There are protocols that have been able to generate TAL from several different reactions, which has driven its price down. TAL is very reactive at several sites on its structure, namely 2 and 4. This project focuses on C-amination at the C-4 position. It was hypothesized that TAL would react to form an amine in a one-step reaction at room temperature in water. We have tested several different amines ranging from basic to aromatic. The mechanism is believed to contain both the keto- and the enol forms of TAL. The amine will react with the keto- form and replace the oxygen with a nitrogen via a Schiff’s base-like process, producing water after condensation. Once the nitrogen is placed on TAL, the structure will tautomerize to form the desired product. The greatest percent yield, 71%, was obtained from Pyrrolidine. 47% and 46% yield respectively were obtained from 4-hydroxybenzyl amine and 3,4,5-trimethylbenzyl amine.

Experimental methodology of C-amination at the C-4 position of triacetic acid lactone

253rd National Meeting (2017)

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