The Journal of Organic Chemistry

An easily introduced and removed protecting group for imidazole nitrogen: a convenient route to 2-substituted imidazoles

NJ Curtis, RS Brown

文献索引：Curtis, N.J.; Brown, R.S. Journal of Organic Chemistry, 1980 , vol. 45, # 20 p. 4038 - 4040

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被引用次数: 93

摘要

Orthoamides (3-5) prepared from imidazoles and triethyl or trimethyl orthoformate are rapidly metalated at-40" C in THF or ether to give the corresponding 2-lithio anion which reacts with a variety of electrophiles. The dialkoxymethyl protecting group is readily hydrolyzed under neutral or acidic conditions at room temperature, giving the 2-substituted 1H-imidazole 1 (R= H, X= COOH, n-C4H9, COCH,, CHOHCsH5, C (CH3) 0H-2-pyridyl, 9-hydroxyfluorenyl, l- ...