IMIDAZOANNELATED IMIDAZOLES: METHODS OF SYNTHESIS AND PRACTICAL APPLICATION
DOI:
https://doi.org/10.32782/pcsd-2021-1-5Keywords:
aminoimidazoles, imidazo[1,2-a]imidazoles, cyclic guanidines, cyclocondensations, biological activityAbstract
In recent decades, the chemistry of imidazoles, which are most likely due to their strong biological potential and practical application, has attracted more and more attention from scientists. The structural fragment of partially hydrogenated imidazoimidazole is an integral part of azamacrocycle precursors such as 1,4,7,10-tetraazacyclododecane and 1,4,7-triazacyclononane, important macrocycles for chelated compounds. The latter, being often paramagnetic materials, are used as contrast agents in magnetic resonance imaging (MRI), as sensitive MRI probes, are used in positron emission tomography (PET), as well as in radioimmunotherapy (RIT). Along with these uses of saturated imidazoimidazole derivatives, they have also been used as ligands in immobilized metal affinity chromatography (IMAC), the most universal method of protein purification. Analysis of the literature has shown that intermolecular cyclocondensations of amino derivatives with a nitrile moiety, intramolecular cyclocondensations of imidazole derivatives and metal-catalytic synthesis are most often used for the synthesis of imidazo[1,2-a]imidazoles. The article provides a comprehensive generalization of the known methods of obtaining imidazoimidazoles, reveals their practical application for both chemistry and medicine.
References
Patent 20050282826 A1 US. Diphenylimidazopyrimidine and -Imidazole Amines as Inhibitors of Beta-Secretase. Publ. 22.12.2005.
Patent 2007145568 A1 WO. Amino-Imidasolines and Their Use as a Medicament for Treating Cognitive Impairment. Alzheimer Disease, Neurodegeneration and Dementia. Publ. 12.06.2007.
Patent 2007145569 A1 WO. Amino-Imidasolines and Their Use as a Medicament for Treating Cognitive Impairment. Alzheimer Disease, Neurodegeneration and Dementia. Publ. 12.06.2007.
Patent 2012112462 A1 WO. Spiro-Amino-Imidazo-Fused Heterocyclic Compounds as Beta-Secretase Modulators and Methods of Use. Publ. 13.02.2012.
Vovk, M.V., Sukach, V.A., Pinchuk, A.M., Chernega, A.N., Pirozhenko, V.V., Howard, J.A. K. Heterocyclization of Functionalized Heterocumulenes with C,N- and C,O-Binucleophiles: V. Synthesis of Imidazo[1,5-a]imidazole Derivatives by Cyclocondensation of 1-Chloroalkyl Isocyanates with Imidazoles and Benzimidazole. Russ. J. Org. Chem. 2004, 40 (11), 1638–1643.
Laroche, C., Kerwin, S.M. Lithiation and Functionalization of 1-Alkynylimidazoles at the 2-Position. Tetrahedron Lett. 2009, 50 (37), 5194–5197.
Zhao, M.-X., Wang, Z.-M., Wang, M.-X., Yan, C.-H., Huang, Z.-T. Reaction of C-Alkylated Heterocyclic Ketene Aminals with Diethyl Azodicarboxylate: Synthesis of Polyfunctionalized Quaternary Carbon Derivatives and Their Thermal Fragmentation. Tetrahedron 2002, 58 (39), 7791–7796.
Laroche, C., Kerwin, S.M. Efficient, Regioselective Access to Bicyclic Imidazo[1,2-x]heterocycles via Gold- and Base-Promoted Cyclization of 1-Alkynylimidazoles. J. Org. Chem. 2009, 74 (23), 9229–9232.
Haslinger, S., Kück, J.W., Anneser, M.R., Cokoja, M., Pöthig, A., Kühn, F.E. Formation of Highly Strained N-Heterocycles via Decomposition of Iron N-Heterocyclic Carbene Complexes: The Value of Labile Fe-C Bonds. Chem. - A Eur. J. 2015, 21 (49), 17860–17869.
Gu, X., Zhang, L., Zhu, X., Wang, S., Zhou, S., Wei, Y., Zhang, G., Mu, X., Huang, Z., Hong, D., et al. Synthesis of Bis(NHC)-Based CNC-Pincer Rare-Earth-Metal Amido Complexes and Their Application for the Hydrophosphination of Heterocumulenes. Organometallics 2015, 34 (18), 4553–4559.
Patent 2005058823 WO. Urea Derivative, Process for Producting the Same, and Use. Publ. 30.08.2006.
Patent 2004048363 WO. Imidazole Derivative, Process for Producing the Same, and Use. Publ. 17.08.2005.
Вайс, Х., Елькманн, В. Глава 18. Функции крови. Физиология человека. Под ред. Р. Шмидта и Г. Тевса. Москва : «Мир», 1996. Т. 2. С. 431–439.
Neuhäuser, C., Reinmuth, M., Kaifer, E., Himmel, H.-J. Synthesis of Oligomeric Zinc Complexes with Bicyclic and Acyclic Guanidinate Ligands. Eur. J. Inorg. Chem. 2012, No. 8, 1250–1260.
Khalaf, M.S., Coles, M.P., Hitchcock, P.B. A Structural, Theoretical and Coordinative Evaluation of the Bicyclic Guanidinate Derived from 1,4,6-Triazabicyclo[3.3.0]oct-4-ene. Dalton Trans. 2008, No. 32, 4288-4295.
