Isoprene-catalyzed lithiation of imidazole: Synthesis of 2-(hydroxyalkyl)- and 2-(aminoalkyl)imidazoles
2-Lithioimidazole was prepared by means of a new protocol, which consists of a slight excess of lithium metal in the presence of a substoichiometric amount of isoprene (20 mol%) in THF at room temperature. By reacting this organolithium with carbonyl elec
Torregrosa, Rosario,Pastor, Isidro M.,Yus, Miguel
p. 11148 - 11155
(2007/10/03)
SYNTHESIS AND APPLICATION OF IMIDAZOLE DERIVATIVES. SYNTHESIS OF (1-METHYL-1H-IMIDAZOL-2-YL)METHANOL DERIVATIVES AND CONVERSION INTO CARBONYL COMPOUNDS
(1-methyl-2H-imidazol-2-yl)methanol derivatives ( 4 and 7 ) were prepared by treating carbonyl compounds with 2-lithio-1-methyl-1H-imidazole ( 2 ) or by treating 2-acyl-1H-imidazoles ( 3 ) with organometallic reagents or sodium borohydride.The alcohols ( 4 and 7 ) were convertible into the carbonyl compounds via the corresponding quaternary salts ( 8 and 10 ).The stable (1-methyl-1H-imidazol-2-yl)methanol system, , can be regarded as a masked form of the carbonyl group as well as a synthon of the group.Keywords - (1-methyl-1H-imidazol-2-yl)methanol; 2-acyl-1-methyl-1H-imidazole; carbonyl compound synthesis; β-ketoester; protecting group; latent functionality; symmetric ketone; dihydrojasmone