Phenylethynyl and Styryl Imidazole Antagonists

Title Phenylethynyl and Styryl Derivatives of Imidazole and Fused Ring Heterocycles 

Invention Significance Glutamate is the major excitatory neurotransmitter 

A solution of 3,5-dimethyl-3H-imidazole-4-carboxylic acid (7.14 mmol) and 1,1 -carbonyl-diimidazole (10.7 mmol) in 35 ml DMF was stirred 3 hours at ambient temperature and then treated with A-hydroxy-acetamidine (9.18 mmol). The mixture was stirred an additional 16 hours at 80°C, then concentrated, and the residue dissolved in 30 ml acetic acid. This mixture was stirred 2 hours at 100°C and was then reconcentrated. The residue was then treated with 50 ml saturated NaHC03 solution and extracted seven times with 30 ml CH2C12. The extracts were washed with 70 ml brine, dried using MgS04, concentrated, and the product isolated in 61% yield as a white solid, mp = 95°C. 

Preparation of 5-(2-bromo-3,5-dimethyl-3H-imidazol-4-yl)-3-methyl-[l,2,4]-oxadiazole 

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