Review
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Year 2022, Volume: 9 Issue: 4, 1335 - 1386, 30.11.2022
https://doi.org/10.18596/jotcsa.1110922

Abstract

References

  • 1. Kochergin PM, Mazur IA, Rogul’chenko GK, Aleksandrova EV, Mandrichenko BE. Studies in the imidazole series. 100. Synthesis of derivatives of imidazo[1,2-a]pyrimidine from 2-aminopyrimidines, methyl aryl ketones, and halogens. Chem Heterocycl Compd. 2000;36(12):1437–40.
  • 2. Saldabol N, Popelis J, Lando O, Slavinska V. 2-(2-furyl) imidazo [1, 2-a] pyrimidine synthesis and electrophilic substitution reactions. Chem Heterocycl Compd. 2006;42(4):495–9.
  • 3. Laquintana V, Denora N, Lopedota A, Suzuki H, Sawada M, Serra M, 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. Bioconjug Chem. 2007 Sep 1;18(5):1397–407.
  • 4. Jensen MS, Hoerrner RS, Li W, Nelson DP, Javadi GJ, Dormer PG, et al. Efficient Synthesis of a GABA A α 2,3 -Selective Allosteric Modulator via a Sequential Pd-Catalyzed Cross-Coupling Approach. J Org Chem. 2005 Jul 1;70(15):6034–9.
  • 5. Blackaby WP, Atack JR, Bromidge F, Castro JL, Goodacre SC, Hallett DJ, et al. Imidazo[1,2-a]pyrimidines as functionally selective GABAA ligands. Bioorg Med Chem Lett. 2006 Mar;16(5):1175–9.
  • 6. Oganisyan AS, Noravyan A, Dzhagatspanyan I, Nazaryan I, Akopyan A. 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. Pharm Chem J. 2007;41(11):588–90.
  • 7. Kiselyov AS, Smith L. Novel one pot synthesis of polysubstituted pyrazolo[1,5-a]- and imidazo[1,2-a]pyrimidines. Tetrahedron Lett. 2006 Apr;47(15):2611–4.
  • 8. Parchinsky VZ, Shuvalova O, Ushakova O, Kravchenko DV, Krasavin M. Multi-component reactions between 2-aminopyrimidine, aldehydes and isonitriles: the use of a nonpolar solvent suppresses formation of multiple products. Tetrahedron Lett. 2006 Feb;47(6):947–51.
  • 9. Jennings ASR, Lewis RT, Russell MGN, Hallett DJ, Street LJ, Castro JL, et al. Imidazo[1,2-b][1,2,4]triazines as α2/α3 subtype selective GABAA agonists for the treatment of anxiety. Bioorg Med Chem Lett. 2006 Mar;16(6):1477–80.
  • 10. Humphries AC, Gancia E, Gilligan MT, Goodacre S, Hallett D, Merchant KJ, 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 GABAA receptor. Bioorg Med Chem Lett. 2006 Mar;16(6):1518–22.
  • 11. Laneri S, Sacchi A, Abignente E. Research on heterocyclic compounds. XLII. The vilsmeier reaction in the synthesis of imidazo[1,2- a ]pyrimidine derivatives. J Heterocycl Chem. 2000 Sep;37(5):1265–7.
  • 12. Elmaati TMA. Reactions with Heterocyclic Amidines: New Routes for the Benzo [4, 5] imidazo [1, 2-a] pyrimidine, Some Pyridine, Pyran and Pyrazole Derivatives Containing the Antipyrine Moiety. Acta Chim Slov. 2002;49:721–32.
  • 13. Sączewski J, Brzozowski Z, Gdaniec M. 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. Tetrahedron. 2005 May;61(22):5303–9.
  • 14. Frohlich J, Sauter F, Chowdhury AS, Hametner C. Reagents for new heteroannelation reactions part V: 2-(methylthio)-2-imidazoline. ARKIVOC. 2000;3:402–8.
  • 15. El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. Solid-phase synthesis of imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines. Tetrahedron Lett. 2003 Aug;44(33):6265–7.
  • 16. Mustazza C, Giudice MRD, Borioni A, Gatta F. 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. J Heterocycl Chem. 2001 Sep;38(5):1119–29.
  • 17. Saldabol NO, Popelis J, Slavinskaya VA. Formylation of furyl-substituted imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine and imidazo[2,1-b]thiazole. Chem Heterocycl Compd. 2001;37(8):1021–4.
  • 18. Bari A, Feist H, Michalik D, Michalik M, Peseke K. Synthesis of Heterocyclic Compounds by Ring Transformations of 2-Formyl Pentose Glycals. Synthesis. 2004 Oct 7;2004(17):2863–8.
  • 19. Majcen-Le Marechal A, Le Grel P, Robert A, Biškup J, Ferk V, Toplak R. Reactivity of 3-halo-2-oxopropanamides and 3-halo-2-cyano-2-hydroxypropanoates: synthesis of S and N containing heterocycles. ARKIVOC. 2001;119:132.
  • 20. Kochergin PM, Mazur IA, Rogul’chenko GK, Aleksandrova EV, Mandrichenko BE. Investigations of Imidazoles. 101. Synthesis of 2,3-Dihydroimidazo[1,2-a]pyrimidine from 2-Aminopyrimidine. Chem Heterocycl Compd. 2001;37(2):224–6.
  • 21. Chowdhury AZMS, Shibata Y. Synthesis of fused pyrimidines with N -, S -heterocyclic moieties by double-annelation reaction. J Heterocycl Chem. 2001 May;38(3):743–7.
  • 22. Adib M, Sheibani E, Bijanzadeh HR, Zhu L-G. 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. Tetrahedron. 2008 Nov;64(47):10681–6.
  • 23. El Otmani B, El Mahi M, Bouhfid R, Essassi EM, Rohand T, Dehaen W, et al. Synthesis of new derivatives of 2, 3-dicyano-imidazo [1, 2-a] pyrimidine from 4-hydroxy-6-methylpyran-2-ones. Arkivoc. 2008;2:59–70.
  • 24. Zhou JP, Ding YW, Zhang HB, Xu L, Dai Y. Synthesis and anti-inflammatory activity of imidazo[1,2-a]pyrimidine derivatives. Chin Chem Lett. 2008 Jun;19(6):669–72.
  • 25. Muzalevskiy V, Nenajdenko V, Shastin A, Balenkova E, Haufe G. Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenes and Their Application in the Synthesis of New Trifluoromethylated Heterocycles. Synthesis. 2009 Jul;2009(13):2249–59.
  • 26. Ermolat’ev DS, Svidritsky EP, Babaev EV, Van der Eycken E. Microwave-assisted synthesis of substituted 2-amino-1H-imidazoles from imidazo[1,2-a]pyrimidines. Tetrahedron Lett. 2009 Sep;50(37):5218–20.
  • 27. Huang W-H, Sheng R, Hu Y-Z. Progress in the Development of Nonpeptidomimetic BACE 1 Inhibitors for Alzheimers Disease. Curr Med Chem. 2009 May 1;16(14):1806–20.
  • 28. Vidal A, Ferrándiz ML, Ubeda A, Acero-Alarcón A, Sepulveda-Arques J, Alcaraz MJ. Effect of imidazo[1,2-α]pyrimidine derivatives on leukocyte function. Inflamm Res. 2001 Jun;50(6):317–20.

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

Year 2022, Volume: 9 Issue: 4, 1335 - 1386, 30.11.2022
https://doi.org/10.18596/jotcsa.1110922

Abstract

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.

References

  • 1. Kochergin PM, Mazur IA, Rogul’chenko GK, Aleksandrova EV, Mandrichenko BE. Studies in the imidazole series. 100. Synthesis of derivatives of imidazo[1,2-a]pyrimidine from 2-aminopyrimidines, methyl aryl ketones, and halogens. Chem Heterocycl Compd. 2000;36(12):1437–40.
  • 2. Saldabol N, Popelis J, Lando O, Slavinska V. 2-(2-furyl) imidazo [1, 2-a] pyrimidine synthesis and electrophilic substitution reactions. Chem Heterocycl Compd. 2006;42(4):495–9.
  • 3. Laquintana V, Denora N, Lopedota A, Suzuki H, Sawada M, Serra M, 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. Bioconjug Chem. 2007 Sep 1;18(5):1397–407.
  • 4. Jensen MS, Hoerrner RS, Li W, Nelson DP, Javadi GJ, Dormer PG, et al. Efficient Synthesis of a GABA A α 2,3 -Selective Allosteric Modulator via a Sequential Pd-Catalyzed Cross-Coupling Approach. J Org Chem. 2005 Jul 1;70(15):6034–9.
  • 5. Blackaby WP, Atack JR, Bromidge F, Castro JL, Goodacre SC, Hallett DJ, et al. Imidazo[1,2-a]pyrimidines as functionally selective GABAA ligands. Bioorg Med Chem Lett. 2006 Mar;16(5):1175–9.
  • 6. Oganisyan AS, Noravyan A, Dzhagatspanyan I, Nazaryan I, Akopyan A. 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. Pharm Chem J. 2007;41(11):588–90.
  • 7. Kiselyov AS, Smith L. Novel one pot synthesis of polysubstituted pyrazolo[1,5-a]- and imidazo[1,2-a]pyrimidines. Tetrahedron Lett. 2006 Apr;47(15):2611–4.
  • 8. Parchinsky VZ, Shuvalova O, Ushakova O, Kravchenko DV, Krasavin M. Multi-component reactions between 2-aminopyrimidine, aldehydes and isonitriles: the use of a nonpolar solvent suppresses formation of multiple products. Tetrahedron Lett. 2006 Feb;47(6):947–51.
  • 9. Jennings ASR, Lewis RT, Russell MGN, Hallett DJ, Street LJ, Castro JL, et al. Imidazo[1,2-b][1,2,4]triazines as α2/α3 subtype selective GABAA agonists for the treatment of anxiety. Bioorg Med Chem Lett. 2006 Mar;16(6):1477–80.
  • 10. Humphries AC, Gancia E, Gilligan MT, Goodacre S, Hallett D, Merchant KJ, 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 GABAA receptor. Bioorg Med Chem Lett. 2006 Mar;16(6):1518–22.
  • 11. Laneri S, Sacchi A, Abignente E. Research on heterocyclic compounds. XLII. The vilsmeier reaction in the synthesis of imidazo[1,2- a ]pyrimidine derivatives. J Heterocycl Chem. 2000 Sep;37(5):1265–7.
  • 12. Elmaati TMA. Reactions with Heterocyclic Amidines: New Routes for the Benzo [4, 5] imidazo [1, 2-a] pyrimidine, Some Pyridine, Pyran and Pyrazole Derivatives Containing the Antipyrine Moiety. Acta Chim Slov. 2002;49:721–32.
  • 13. Sączewski J, Brzozowski Z, Gdaniec M. 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. Tetrahedron. 2005 May;61(22):5303–9.
  • 14. Frohlich J, Sauter F, Chowdhury AS, Hametner C. Reagents for new heteroannelation reactions part V: 2-(methylthio)-2-imidazoline. ARKIVOC. 2000;3:402–8.
  • 15. El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. Solid-phase synthesis of imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines. Tetrahedron Lett. 2003 Aug;44(33):6265–7.
  • 16. Mustazza C, Giudice MRD, Borioni A, Gatta F. 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. J Heterocycl Chem. 2001 Sep;38(5):1119–29.
  • 17. Saldabol NO, Popelis J, Slavinskaya VA. Formylation of furyl-substituted imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine and imidazo[2,1-b]thiazole. Chem Heterocycl Compd. 2001;37(8):1021–4.
  • 18. Bari A, Feist H, Michalik D, Michalik M, Peseke K. Synthesis of Heterocyclic Compounds by Ring Transformations of 2-Formyl Pentose Glycals. Synthesis. 2004 Oct 7;2004(17):2863–8.
  • 19. Majcen-Le Marechal A, Le Grel P, Robert A, Biškup J, Ferk V, Toplak R. Reactivity of 3-halo-2-oxopropanamides and 3-halo-2-cyano-2-hydroxypropanoates: synthesis of S and N containing heterocycles. ARKIVOC. 2001;119:132.
  • 20. Kochergin PM, Mazur IA, Rogul’chenko GK, Aleksandrova EV, Mandrichenko BE. Investigations of Imidazoles. 101. Synthesis of 2,3-Dihydroimidazo[1,2-a]pyrimidine from 2-Aminopyrimidine. Chem Heterocycl Compd. 2001;37(2):224–6.
  • 21. Chowdhury AZMS, Shibata Y. Synthesis of fused pyrimidines with N -, S -heterocyclic moieties by double-annelation reaction. J Heterocycl Chem. 2001 May;38(3):743–7.
  • 22. Adib M, Sheibani E, Bijanzadeh HR, Zhu L-G. 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. Tetrahedron. 2008 Nov;64(47):10681–6.
  • 23. El Otmani B, El Mahi M, Bouhfid R, Essassi EM, Rohand T, Dehaen W, et al. Synthesis of new derivatives of 2, 3-dicyano-imidazo [1, 2-a] pyrimidine from 4-hydroxy-6-methylpyran-2-ones. Arkivoc. 2008;2:59–70.
  • 24. Zhou JP, Ding YW, Zhang HB, Xu L, Dai Y. Synthesis and anti-inflammatory activity of imidazo[1,2-a]pyrimidine derivatives. Chin Chem Lett. 2008 Jun;19(6):669–72.
  • 25. Muzalevskiy V, Nenajdenko V, Shastin A, Balenkova E, Haufe G. Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenes and Their Application in the Synthesis of New Trifluoromethylated Heterocycles. Synthesis. 2009 Jul;2009(13):2249–59.
  • 26. Ermolat’ev DS, Svidritsky EP, Babaev EV, Van der Eycken E. Microwave-assisted synthesis of substituted 2-amino-1H-imidazoles from imidazo[1,2-a]pyrimidines. Tetrahedron Lett. 2009 Sep;50(37):5218–20.
  • 27. Huang W-H, Sheng R, Hu Y-Z. Progress in the Development of Nonpeptidomimetic BACE 1 Inhibitors for Alzheimers Disease. Curr Med Chem. 2009 May 1;16(14):1806–20.
  • 28. Vidal A, Ferrándiz ML, Ubeda A, Acero-Alarcón A, Sepulveda-Arques J, Alcaraz MJ. Effect of imidazo[1,2-α]pyrimidine derivatives on leukocyte function. Inflamm Res. 2001 Jun;50(6):317–20.
There are 28 citations in total.

Details

Primary Language English
Subjects Inorganic Chemistry
Journal Section REVIEW ARTICLES
Authors

Rabia Zeynep Kobak 0000-0001-9140-7487

Barbaros Akkurt 0000-0003-4066-3004

Publication Date November 30, 2022
Submission Date April 29, 2022
Acceptance Date October 10, 2022
Published in Issue Year 2022 Volume: 9 Issue: 4

Cite

Vancouver Kobak RZ, Akkurt B. Formation and Uses of Imidazo[1,2-a]pyrimidines and Related Compounds: A Review Comprising Years 2000-2021. JOTCSA. 2022;9(4):1335-86.