Fujita Hikaru, Yagitani Tomomi, Kunishima Munetaka
Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima, Chuo-ku, Kobe, Hyogo 650-8586, Japan.
J Org Chem. 2024 Oct 18;89(20):15302-15306. doi: 10.1021/acs.joc.4c01406. Epub 2024 Oct 1.
,-Dimethylated (alkoxy)triazinediones (DMATs-R) with eight different -alkyl groups (R), such as benzyl, allyl, and -butyl groups, were synthesized in 61-94% yield through the alkoxy exchange reaction of DMAT-Me with the corresponding alcohol. Molecular sieves were added to the reaction mixture to shift the alkoxy exchange equilibrium toward the product via the absorptive removal of the methanol formed . All the DMATs-R were obtained as stable solids, in contrast to previously reported ,-diallyl analogs that included oil compounds. The treatment of alcohols with DMATs-R in the presence of an acid catalyst afforded the corresponding alkyl ethers in up to 92% yield. A base-labile bromoalkyl group is compatible with these reactions. The --butylation of a sterically hindered -alcohol with DMAT-Bu yielded the di--butyl ether product. The DMATs-R are suitable reagents for the -alkylative protection of alcohols under nonbasic conditions.
