A. Shahrisa, R. Tabrizi, H. R. Ahsani
Feb 1, 2000
Citations
0
Influential Citations
7
Citations
Journal
Organic Preparations and Procedures International
Abstract
4H-Pyran-4-ones are heterocycles with useful biological properties.’ These compounds are valuable as fungicides, herbicides and in the treatment of hypersensitivity conditions, such as asthma and allergies.? Functionalized heterocycles are often used for the synthesis of the target organic compounds. The synthesis of 2-bromomethyl-6-methyl-4H-pyran-4-one (2b) was reported by BuuHoi” and Yamamoto4 in low yields. Both of these groups were only able to document the formation of the compound and the published data on this method is very misleading. Bromination of 2,6dimethyl-4H-pyran-4-one (1) with two equivalents of N-bromosuccinimide in the presence of dibenzoyl peroxide in tetrachloromethane led to six brominated compounds 2a-f, in very small yields and after a very tedious and long acquisition time (Scheme