Formation and Uses of Imidazo[1,2-a]pyrimidines and Related Compounds: A Review Comprising Years 2000-2021

This work covers the selected synthetic papers of imidazo[1,2-a]pyrimidine and its derivatives between the years 2000 and 2021. Synthesis of the heterocyclic moiety, application of this scaffold to biological activities, and secondary applications like corrosion inhibition are provided. The authors hope that readers will find the treatise useful.

[1]  V. Rusinov,et al.  Benzimidazoazapurines: Design, Synthesis, and Photophysical Study. , 2021, The Journal of organic chemistry.

[2]  Anamika,et al.  Ferrocene-Functionalized Dithiocarbamate Zinc(II) Complexes as Efficient Bifunctional Catalysts for the One-Pot Synthesis of Chromene and Imidazopyrimidine Derivatives via Knoevenagel Condensation Reaction. , 2021, Inorganic chemistry.

[3]  M. Ghasemzadeh,et al.  Fe3O4@TiO2@ILs-ZIF-8 Nanocomposite: A Robust Catalyst for the Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidines , 2021, Journal of Molecular Structure.

[4]  Tuğba GÜngÖr.  Microwave assisted, sequential two-step, one-pot synthesis of novel imidazo[1,2-a]pyrimidine containing tri/tetrasubstituted imidazole derivatives , 2021, Turkish journal of chemistry.

[5]  A. Marsaioli,et al.  Fluorescent Imidazo[1,2-a]pyrimidine Compounds as Biocompatible Organic Photosensitizers that Generate Singlet Oxygen: A Potential Tool for Phototheranostics. , 2020, Chemistry.

[6]  Om P. S. Patel,et al.  Recent Advances in Radical C−H Bond Functionalization of Imidazoheterocycles , 2020 .

[7]  A. Zarghi,et al.  Novel 4-Oxo-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylic Acid Derivatives as HIV-1 Integrase Inhibitors: Synthesis, Docking studies, Molecular Dynamics Simulation and Biological Activities. , 2020, Medicinal chemistry (Shariqah (United Arab Emirates)).

[8]  F. Gosselin,et al.  Practical Synthesis of a Stable Precursor for Positron Emission Tomography Imaging Agent 18F-GTP1 , 2020 .

[9]  Shutao Ma,et al.  Recent Development of Pyrimidine‐Containing Antimicrobial Agents , 2020, ChemMedChem.

[10]  Megha Rai,et al.  Synthesis of substituted pyrimidine using ZnFe 2 O 4 nanocatalyst via one pot multi‐component reaction ultrasonic irradiation , 2020 .

[11]  M. Naimi-Jamal,et al.  Novel magnetic propylsulfonic acid-anchored isocyanurate-based periodic mesoporous organosilica (Iron oxide@PMO-ICS-PrSO3H) as a highly efficient and reusable nanoreactor for the sustainable synthesis of imidazopyrimidine derivatives , 2020, Scientific Reports.

[12]  Renata A. Balaguez,et al.  Trihaloisocyanuric acids in ethanol: an eco-friendly system for the regioselective halogenation of imidazo-heteroarenes , 2020 .

[13]  Tuğba GÜngÖr.  One pot, multicomponent protocol for the synthesis of novel imidazo[1,2-a]pyrimidine-based pyran analogs: a potential biological scaffold , 2020, Monatshefte für Chemie - Chemical Monthly.

[14]  E. Novellino,et al.  Targeting the KRAS Oncogene: Synthesis, Physicochemical and Biological Evaluation of Novel G-Quadruplex DNA Binders. , 2020, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[15]  V. Srivastava,et al.  Starch functionalized magnetite nanoparticles: A green, biocatalyst for one-pot multicomponent synthesis of imidazopyrimidine derivatives in aqueous medium under ultrasound irradiation , 2020 .

[16]  M. H. El-Hamamsy,et al.  Design, synthesis, and bioactivity of dihydropyrimidine derivatives as kinesin spindle protein inhibitors. , 2019, Bioorganic & medicinal chemistry.

[17]  L. Puskás,et al.  A convenient approach for the preparation of imidazo[1,2-a]-fused bicyclic frameworks via IBX/NIS promoted oxidative annulation. , 2019, Organic & biomolecular chemistry.

[18]  R. Lytvyn,et al.  4-(4-Acethylphenyl)-3-hydroxycoumarin in the Synthesis of Nitrogen-containing Heterocycles with a Neoflavonoid Moiety , 2019, Russian Journal of Organic Chemistry.

[19]  K. El-Bayouki,et al.  Silica sulfuric acid/ethylene glycol as an efficient catalyst for the synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine-3-carbonitrile derivatives , 2019, Synthetic Communications.

[20]  P. Maji.  Synthesis of Pyrimidine-Annulated Five-Membered Heterocycles: An Overview , 2019 .

[21]  H. Katouah,et al.  Synthesis of Pyrimidine and Pyran Derivatives with the Related Systems and the Study of Their Behavior in the Liquid Solutions , 2019, Journal of Heterocyclic Chemistry.

[22]  R. Gundla,et al.  Rational design, molecular docking and synthesis of novel homopiperazine linked imidazo[1,2-a]pyrimidine derivatives as potent cytotoxic and antimicrobial agents. , 2019, Bioorganic & medicinal chemistry letters.

[23]  R. Lytvyn,et al.  Synthesis and Antimicrobial Activity of 3-Phenyl-1-Methylquinolin-2-One Derivatives , 2019, Pharmaceutical Chemistry Journal.

[24]  A. Farag,et al.  Synthesis, biological evaluation and DFT calculation of novel pyrazole and pyrimidine derivatives , 2019, Journal of Molecular Structure.

[25]  R. Shrivastava,et al.  A new insight into corrosion inhibition mechanism of copper in aerated 3.5 wt.% NaCl solution by eco-friendly Imidazopyrimidine Dye: experimental and theoretical approach , 2019, Chemical Engineering Journal.

[26]  Naeemah Al-lami,et al.  Pryparation, Characterization And Biological Activity of New Derivatives of 2-Biphenyl-3-Aminomethylimidazo(1,2- a)Pyrimidine , 2019 .

[27]  S. A. Pourmousavi,et al.  Sulfonic Acid-Functionalized Magnetic Nanoparticles as an Efficient Catalyst for the Synthesis of Benzo[4, 5]imidazo[1, 2-a]pyrimidine Derivatives, 2-Aminobenzothia Zolomethylnaphthols and 1-Amidoalkyl-2-naphthols. , 2019, Current organic synthesis.

[28]  A. L. Braga,et al.  NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions , 2018, Tetrahedron.

[29]  D. Rawat,et al.  Copper oxide nanoparticle catalysed synthesis of imidazo[1,2-a]pyrimidine derivatives, their optical properties and selective fluorescent sensor towards zinc ion , 2018, Tetrahedron Letters.

[30]  Jessy Aziz,et al.  An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles , 2017, Synthesis.

[31]  V. Telvekar,et al.  NBS mediated protocol for the synthesis of N-bridged fused heterocycles in water , 2017 .

[32]  Dong Wook Kim,et al.  Polyethylene glycol methacrylate-grafted dicationic imidazolium-based ionic liquid: Heterogeneous catalyst for the synthesis of aryl-benzo[4,5]imidazo[1,2-a]pyrimidine amines under solvent-free conditions , 2017 .

[33]  T. Ben Hadda,et al.  In vitro anti-Giardia lamblia activity of 2-aryl-3-hydroxymethyl imidazo[1,2-a]pyridines and -pyrimidines, individually and in combination with albendazole. , 2016, Acta tropica.

[34]  D. Matosiuk,et al.  Structural investigations of a series of 1,6-aryl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-ones with potential antinociceptive activity , 2015 .

[35]  N. Jain,et al.  Synthesis and antiproliferative activity of imidazo[1,2-a]pyrimidine Mannich bases. , 2015, European journal of medicinal chemistry.

[36]  H. Moustafa,et al.  Electronic spectra and DFT calculations of some pyrimido[1,2-a]benzimidazole derivatives. , 2015, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[37]  A. Mehranpour,et al.  Synthesis and Characterization of New Benzimidazole Derivatives Using 2‐Substituted 1,3‐Bis(dimethylamino)‐trimethinium Salts. , 2014 .

[38]  B. Cosimelli,et al.  Synthesis and biological evaluation of imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyridines as new inhibitors of the Wnt/β-catenin signaling. , 2014, European journal of medicinal chemistry.

[39]  M. M. Burbulienė.  Interaction of methyl (2-methylsulfanyl-6-phenyl-4- thioxopyrimidin-3(4H)-yl)acetate with hydrazine hydrate , 2014 .

[40]  Lihong Hu,et al.  Facile and Green Method for the Synthesis of 4-Amino-1,2-Dihydrobenzo [4,5]Imidazo[1,2-a]Pyrimidine-3-Carbonitriles Catalysed by Ammonium Acetate , 2012 .

[41]  B. Hammouti,et al.  Comparative Study of Pyridine and Pyrimidine Derivatives as Corrosion Inhibitors of C38 Steel in Molar HCl , 2012, International Journal of Electrochemical Science.

[42]  Jianquan Hong,et al.  An Efficient and Clean CuI-Catalyzed Chalcogenylation of Aromatic Azaheterocycles with Dichalcogenides. , 2011 .

[43]  Raed A. Al‐Qawasmeh,et al.  Post Groebke-Blackburn multicomponent protocol: synthesis of new polyfunctional imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine derivatives as potential antimicrobial agents. , 2010, European journal of medicinal chemistry.

[44]  Q. You,et al.  Design, synthesis and bioevaluation of dihydropyrazolo[3,4-b]pyridine and benzo[4,5]imidazo[1,2-a]pyrimidine compounds as dual KSP and Aurora-A kinase inhibitors for anti-cancer agents. , 2010, Bioorganic & medicinal chemistry.

[45]  V. Nenajdenko,et al.  Synthetic Approach to Alkoxy‐β‐(trifluoromethyl)styrenes and Their Application in the Synthesis of New Trifluoromethylated Heterocycles. , 2009 .

[46]  E. V. D. Eycken,et al.  Microwave-assisted synthesis of substituted 2-amino-1H-imidazoles from imidazo[1,2-a]pyrimidines , 2009 .

[47]  V. Nenajdenko,et al.  Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenesand Their Application in the Synthesis of New TrifluoromethylatedHeterocycles , 2009 .

[48]  Yongzhou Hu,et al.  Progress in the development of nonpeptidomimetic BACE 1 inhibitors for Alzheimer's disease. , 2009, Current medicinal chemistry.

[49]  M. Adib,et al.  A new, one-pot, multi-component synthesis of imines of 3-amino-2-arylimidazo[1,2-a]pyridines, 3-amino-2-arylimidazo[1,2-a]pyrazines, and 3-amino-2-arylimidazo[1,2-a]pyrimidines , 2008 .

[50]  Huibin Zhang,et al.  Synthesis and anti-inflammatory activity of imidazo[1,2-a]pyrimidine derivatives , 2008 .

[51]  I. A. Dzhagatspanyan,et al.  Derivatives of condensed thienopyrimidines: Synthesis and anticonvulsant and tranquilizer activity of hydrochlorides of pyrano[4′,3′:4,5]thieno[3,2-e]imidazo[1,2-a]pyrimidines , 2007, Pharmaceutical Chemistry Journal.

[52]  W. Dehaen,et al.  Synthesis of new derivatives of 2,3-dicyano-imidazo[1,2-a]pyrimidine from 4-hydroxy-6-methylpyran-2-ones , 2007 .

[53]  G. Biggio,et al.  N-benzyl-2-(6,8-dichloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(6-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)hexyl)acetamide as a new fluorescent probe for peripheral benzodiazepine receptor and microglial cell visualization. , 2007, Bioconjugate chemistry.

[54]  A. Kiselyov,et al.  Novel one pot synthesis of polysubstituted pyrazolo[1,5-a]- and imidazo[1,2-a]pyrimidines , 2006 .

[55]  J. Popelis,et al.  2-(2-furyl)imidazo[1,2-a]pyrimidine synthesis and electrophilic substitution reactions , 2006 .

[56]  S. Tye,et al.  Imidazo[1,2-b][1,2,4]triazines as α2/α3 subtype selective GABAA agonists for the treatment of anxiety , 2006 .

[57]  E. Gancia,et al.  8-Fluoroimidazo[1,2-a]pyridine: synthesis, physicochemical properties and evaluation as a bioisosteric replacement for imidazo[1,2-a]pyrimidine in an allosteric modulator ligand of the GABA A receptor. , 2006, Bioorganic & medicinal chemistry letters.

[58]  A. Pike,et al.  Imidazo[1,2-a]pyrimidines as functionally selective GABA(A) ligands. , 2006, Bioorganic & medicinal chemistry letters.

[59]  Olga Shuvalova,et al.  Multi-component reactions between 2-aminopyrimidine, aldehydes and isonitriles : the use of a nonpolar solvent suppresses formation of multiple products , 2006 .

[60]  D. Cai,et al.  Efficient synthesis of a GABA A alpha2,3-selective allosteric modulator via a sequential Pd-catalyzed cross-coupling approach. , 2005, The Journal of organic chemistry.

[61]  M. Gdaniec,et al.  Synthesis of 2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-ones by the domino Michael addition retro-ene reaction of 2-alkoxyiminoimidazolidines and acetylene carboxylates , 2005 .

[62]  D. Michalik,et al.  Synthesis of Heterocyclic Compounds by Ring Transformations of 2-Formyl Pentose Glycals. , 2005 .

[63]  D. Michalik,et al.  Synthesis of heterocyclic compounds by ring transformations of 2-formyl pentose glycals , 2004 .

[64]  A. Katritzky,et al.  Regiospecific Synthesis of 3‐Substituted Imidazo[1,2‐a]pyridines, Imidazo[1,2‐a]pyrimidines, and Imidazo[1,2‐c]pyrimidine. , 2003 .

[65]  A. L. Marechal,et al.  Reactivity of 3-halo-2-oxopropanamides and 3-halo-2-cyano-2- hydroxypropanoates: synthesis of S and N containing heterocycles , 2002 .

[66]  T. M. A. Elmaati.  Reactions with heterocyclic amidines: New routes for the synthesis of novel azolo[1,5-a]pyrimidine, benzo[4,5]imidazo[1,2-a]pyrimidine, some pyridine, pyran and pyrazole derivatives containing the antipyrine moiety , 2002 .

[67]  A. Borioni,et al.  Synthesis of pyrazolo[1,5‐a]‐, 1,2,4‐triazolo[1,5‐a]‐ and imidazo[1,2‐a]pyrimidines related to zaleplon, a new drug for the treatment of insomnia , 2001 .

[68]  J. Popelis,et al.  Formylation of Furyl-substituted Imidazo[1,2-a]pyridine, Imidazo[1,2-a]pyrimidine and Imidazo[2,1-b]thiazole , 2001 .

[69]  M. Alcaraz,et al.  Effect of imidazo[1,2-α]pyrimidine derivatives on leukocyte function , 2001, Inflammation Research.

[70]  Y. Shibata,et al.  Synthesis of fused pyrimidines with N‐, S‐heterocyclic moieties by double‐annelation reaction , 2001 .

[71]  E. Aleksandrova,et al.  Investigations of Imidazoles. 101. Synthesis of 2,3-Dihydroimidazo[1,2-a]pyrimidine from 2-Aminopyrimidine , 2001 .

[72]  S. Laneri,et al.  Research on heterocyclic compounds. XLII. The vilsmeier reaction in the synthesis of imidazo[1,2‐a]pyrimidine derivatives , 2000 .

[73]  C. Hametner,et al.  Reagents for new heteroannelation reactions part V: 2-(methylthio)-2-imidazoline , 2000 .