通过 1,2,3-三嗪与仲胺反应直接合成β-氨基酸醛。
Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.
机构信息
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.
出版信息
Org Lett. 2017 Jul 7;19(13):3568-3571. doi: 10.1021/acs.orglett.7b01543. Epub 2017 Jun 28.
Abstract
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.
摘要
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。
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