A facile preparation of various N-heterocycles using amides and olefins

作者：Gratia Synthia S; Vigneau Edward S; Eltayeb Sumiea; Patel Kishan; Meyerhoefer Terence J; Kershaw Sonia; Huang Victor; De Castro Michael^*

来源：Tetrahedron Letters, 2014, 55(2): 448-452.

DOI：10.1016/j.tetlet.2013.11.054

• Heterocycles
• Carbohydrates
• Olefins
• Oxazolines
• Amides

We herein report a one pot approach for the synthesis of various nitrogen containing heterocycles including: oxazolines, thiazolines, and dihydro dioxazines via the addition of amides to olefins in the presence of N-iodosuccinimide (NIS) and propionitrile at high temperatures. Thus, the reaction of aryl/heteroaryl amides, thioamides, N-hydroxybenzamide, and phenylurea with various olefins in the presence of NIS and propionitrile at 45 degrees C afforded the N-heterocycles in good to moderate yields. Reaction of the electron deficient tri-O-acetyl-D-glucal and tri-O-acetyl-D-galactal with benzamide and thiophene-2-carboxamide afforded the N-glycooxazolines in good yields. The newly made heterocycles were tested against various enzymes. Only 3,6-diphenyl-dihydro-1,4,2-dioxazine (1c) was found to moderately inhibit hexokinase II (hHI(2).

• 出版日期2014-1-8