N-Methylimidazole: Attractive and Valuable Chameleonic Species

Introduction

In the last decades N-methylimidazole (N-Mim) has attracted the attention of a great number of research groups due to its broad chameleonic behavior, being widely used in organic chemistry as a solvent, as co-catalyst, ligand in metal complexes, Brønsted or Lewis base catalyst. N-Mim participates in the active center of several enzymes, as an ionic liquid precursor, as electron acceptor or as key intermediate in synthesis. [¹-7] On the other hand, the chemistry of imidazole compounds in general has been also a center of interest due to the presence of its essential functional unit in a large variety of biological important molecules, being the N-methylimidazole used to mimic aspects of several of these biomolecules. [8] These derivatives can be helpful in studies to elucidate biological mechanisms, and its importance has led to several international patents. The different roles played by N-methylimidazole have been extensively applied for the synthesis of important targets. [8]

References

• 1 Yavari I. Hossaini Z. Souri S. Sabbaghan M. Synlett  2008,  1287 
• 2 Liu BK. Wu Q. Qian XQ. Lv DS. Lin XF. Synthesis  2007,  2653 
• 3 Li J. Hu F. Xie X.-K. Liu F. Huang Z.-Z. Catal. Commun.  2009,  11:  276 
• 4 Jadhav VH. Jeong H.-J. Lim ST. Sohn M.-H. Kim DW. Org. Lett.  2011,  13:  2502 
• 5 Liu B.-K. Wu Q. Xu J.-M. Lin X.-F. Chem. Commun.  2007,  295 
• 6 Xie C. Zhang Y. Org. Lett.  2007,  9:  781 
• 7 Carcedo C. Knight JC. Pope SJA. Fallis IA. Dervisi A. Organometallics  2011,  30:  2553 
• 8a Kashiwazaki G. Bando T. Shinohara K.-i. Minoshima M. Kumamoto H. Nishijima S. Sugiyama H. Bioorg. Med. Chem.  2010,  18:  2887 
• 8b Kraus JM. Tatipaka HB. McGuffin SA. Chennamaneni NK. Karimi M. Arif J. Verlinde CLMJ. Buckner FS. Gelb MH. J. Med. Chem.  2010,  53:  3887 
• 8c Jablonowski JA. Ly KS. Bogenstaetter M. Dvorak CA. Boggs JD. Dvorak LK. Lord B. Miller KL. Mazur C. Wilson SJ. Lovenberg TW. Carruthers NI. Bioorg. Med. Chem. Lett.  2009,  19:  903 
• 8d Su W. Gray SJ. Dondi R. Burley GA. Org. Lett.  2009,  11:  3910 
• 9 Ebel K. Koehler H. Gamer AO. Jäckh R. Imidazole and Derivatives, In Ullmann’s Encyclopedia of Industrial Chemistry   Wiley-VCH; Weinheim: 2002.