Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Org Lett. 2017 Jul 7;19(13):3568-3571. doi: 10.1021/acs.orglett.7b01543. Epub 2017 Jun 28.
Simple and direct nucleophilic addition of secondary amines, including imidazole, to 1,2,3-triazine under mild reaction conditions (THF, 25-65 °C, 12-48 h), requiring no additives, cleanly provides β-aminoenals 4 in good yields (21 examples, 31-79%). The reaction proceeds by amine nucleophilic addition to C4 of the 1,2,3-triazine, in situ loss of N, and subsequent imine hydrolysis to provide 4.
在温和的反应条件下(THF,25-65°C,12-48 小时),仲胺(包括咪唑)可简单直接地与 1,2,3-三嗪发生亲核加成反应,无需添加任何助剂,以良好的收率(21 个实例,31-79%)得到β-氨基醛 4。该反应通过胺对 1,2,3-三嗪的 C4 位的亲核加成、原位失去 N 和随后的亚胺水解进行,得到 4。