Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5263907 | Tetrahedron Letters | 2014 | 5 Pages |
Abstract
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 °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 (hHK2).
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Synthia S. Gratia, Edward S. Vigneau, Sumiea Eltayeb, Kishan Patel, Terence J. Meyerhoefer, Sonia Kershaw, Victor Huang, Michael De Castro,