69840-48-8Relevant articles and documents
Direct C-N coupling of imidazoles and benzylic compounds via iron-catalyzed oxidative activation of C-H bonds
Xia, Qinqin,Chen, Wanzhi,Qiu, Huayu
experimental part, p. 7577 - 7582 (2011/11/12)
Iron-catalyzed direct C-N bond formation between imidazoles and benzylic hydrocarbons is described. The reaction utilizes an inexpensive iron catalyst-oxidant system that is suitable for the coupling of a range of benzylic C-H bonds with various imidazoles.
Chiral azole derivatives. 2. Synthesis of enantiomerically pure 1-alkylimidazoles
Corelli,Summa,Brogi,Monteagudo,Botta
, p. 2008 - 2015 (2007/10/02)
4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benzhydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-α-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.