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A novel class of extended pi-conjugated systems: one-pot synthesis of bis-3-aminoimidazo[1,2-a]pyridines, pyrimidines and pyrazines

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Abstract

Bis-3-aminoimidazo[1, 2-a] pyridines, pyrimidines and pyrazines as extended pi-conjugated systems were synthesized for the first time by a novel pseudo five-component condensation of 2-aminopyridine pyrimidines and pyrazines derivatives with terephthalaldehyde or isophthalaldehyde and isocyanides in the presence of p-toluenesulfonic acid in methanol.

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References

  1. Terrett NK (1998) Combinatorial chemistry. Oxford University Press, New York

    Google Scholar 

  2. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39: 3168–3210 doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U

    Article  Google Scholar 

  3. Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106: 17–89. doi:10.1021/cr0505728

    Article  PubMed  CAS  Google Scholar 

  4. Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley-VCH, Weinheim

  5. Bienayme H, Hulme C, Oddon G, Schmidt P (2000) Maximizing synthetic efficiency: multi-component transformations lead the way. Chem Eur J 6: 3321–3329 doi:10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A

    Article  CAS  Google Scholar 

  6. Hulme C, Morrissette MM, Volz FA, Burns CJ (1998) The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: novel application of Armstrong’s convertible isonitrile. Tetrahedron Lett 39: 1113–1116. doi:10.1016/S0040-4039(97)10795-X

    Article  CAS  Google Scholar 

  7. Hulme C, Gore V (2003) Multi-component reactions: emerging chemistry in drug discovery ‘from xylocain to crixivan’ Curr Med Chem 10: 51–80. doi:10.2174/0929867033368600

    Article  PubMed  CAS  Google Scholar 

  8. Schwerkoske J, Masquelin T, Perun T, Hulme C (2005) New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines. Tetrahedron Lett 46: 8355–8357. doi:10.1016/j.tetlet.2005.09.181

    Article  CAS  Google Scholar 

  9. Trapani G, Franco M, Ricciardi L, Latrofa A, Genchi G, Sanna E, Tuveri F, Cagetti E, Biggio G, Liso G (1997) Synthesis and binding affinity of 2-phenylimidazo[1,2-a]pyridine derivatives for both central and peripheral benzodiazepine receptors. A new series of high-affinity and selective ligands for the peripheral type. J Med Chem 40: 3109–3118. doi:10.1021/jm970112+

    Article  PubMed  CAS  Google Scholar 

  10. Hamdouchi C, de Blas J, del Prado M, Gruber J, Heinz BA, Vance L (1999) 2-Amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl) vinyl]imidazo[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus: stereospecific synthesis and antiviral activity. J Med Chem 42: 50–59. doi:10.1021/jm9810405

    Article  PubMed  CAS  Google Scholar 

  11. Gueiffier A, Mavel S, Lhassani M, Elhakmaoui A, Snoeck R, Andrei G, Chavignon O, Teulade JC, Witvrouw M, Balzarini J, De Clercq E, Chapat JP (1998) Synthesis of imidazo[1,2-a]pyridines as antiviral agents. J Med Chem 41: 5108–5112. doi:10.1021/jm981051y

    Article  PubMed  CAS  Google Scholar 

  12. Mosby WL (1961) Fused 6/6 ring systems with one extra heteroatom. In: Mosby WL (ed) Heterocyclic systems with bridgehead nitrogen atoms. Wiley, New York, Part I, p 460 and Part II, p 802

  13. Blewitt HL (1977) Indolizine & aza derivatives with additional nitrogens in the 5-membered ring. In: Weissberger A, Taylor EC(eds) Special topics in heterocyclic chemistry. Wiley, New York, p 117

    Google Scholar 

  14. Spitzer WA, Victor F, Pollock DG, Hayers JS (1988) Imidazo[ 1,2-a ]pyrimidines and imidazo[ 1,2-a ipyrazines: the role of nitrogen position in inotropic activity. J Med Chem 31: 1590–1595. doi:10.1021/jm00403a018

    Article  PubMed  CAS  Google Scholar 

  15. Blackburn C, Guan B (2000) A novel dealkylation affording 3-aminoimidazo[1,2-a]pyridines: access to new substitution patterns by solid-phase synthesis. Tetrahedron Lett 41: 1495–1500. doi:10.1016/S0040-4039(00)00003-4

    Article  CAS  Google Scholar 

  16. Blackburn C (1998) A three-component solid-phase synthesis of 3-aminoimidazo[l,2-a]azines. Tetrahedron Lett 39: 5469–5472. doi:10.1016/S0040-4039(98)01113-7

    Article  CAS  Google Scholar 

  17. Bienayme’ H, Bouzid K (1998) A new heterocyclic multicom- ponent reaction for the combinatorial synthesis of fused 3-ami- noimidazoles. Angew Chem Int Ed 37: 2234–2237 doi:10.1002/(SI CI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO; 2-R

    Article  Google Scholar 

  18. Groebke K, Weber L, Mehlin F (1998) Synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines by a novel three-component condensation. Synlett 661–663. doi:10.1055/s-1998-1721

  19. Mandair GS, Light M, Russell A, Hursthouse M, Bradley M (2002) Re-evaluation of the outcome of a multiple component reaction—2- and 3-amino-imidazo[1,2-a]pyrimidines. Tetrahedron Lett 43: 4267–4269. doi:10.1016/S0040-4039(02)00709-8

    Article  CAS  Google Scholar 

  20. Irie M (1994) Photo-reactive materials for ultrahigh-density optical memory. Elsevier, Amsterdam, The Netherlands

    Google Scholar 

  21. Feringa BL (2001) Molecular switches. Weinheim, Wiley-VCH, Germany doi:10.1002/3527600329

    Book  Google Scholar 

  22. Dürr H, Bouus-Laurent H (1990) Photochromism: molecules and systems. Elsevier, Amsterdam, The Netherlands

    Google Scholar 

  23. Shaabani A, Soleimani E, Maleki A (2006) Ionic liquid promoted one-pot. synthesis of 3-aminoimidazo[1,2-a]pyridines. Tetrahedron Lett 47: 3031–3034. doi:10.1016/j.tetlet.2006.03.011

    Article  CAS  Google Scholar 

  24. Shaabani A, Soleimani E, Rezayan AH (2007) A novel approach for the synthesis of alkyl and aryl sulfonamides. Tetrahedron Lett 48: 2185–2188. doi:10.1016/j.tetlet.2007.01.091

    Article  CAS  Google Scholar 

  25. Shaabani A, Soleimani E, Khavasi HR, Hoffmann RD, Rodewald UC, Poättgen R (2006) An isocyanide-based three-component reaction: synthesis of fully substituted N-alkyl-2-triphenylphosphoranylidene glutarimides. Tetrahedron Lett 47: 5493–5496. doi:10.1016/j.tetlet.2006.05.164

    Article  CAS  Google Scholar 

  26. Shaabani A, Maleki A, Moghimi-Rad J (2007) A novel isocyanide-based three-component reaction: synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives. J Org Chem 72: 6309–6311. doi:10.1021/jo0707131

    Article  PubMed  CAS  Google Scholar 

  27. Shaabani A, Maleki A, Mofakham H, Khavasi HR (2008) Novel isocyanide-based three-component synthesis of 3,4-dihydroquinoxalin-2-amine derivatives. J Comb Chem 10: 323–325. doi:10.1021/cc7001777

    Article  PubMed  CAS  Google Scholar 

  28. Shaabani A, Maleki A, Mofakham H, Moghimi-Rad J (2008) A novel one-pot pseudo-five-component synthesis of 4,5,6,7-tetrahydro-1H-1,4-diazepine-5-carboxamide derivatives. J Org Chem 73: 3925–3927. doi:10.1021/jo8002612

    Article  PubMed  CAS  Google Scholar 

  29. Shaabani A, Maleki A, Mofakham H (2008) Novel multicomponent one-pot synthesis of tetrahydro-1H-1,5-benzodiazepine- 2-carboxamide derivatives. J Comb Chem 10: 595–598. doi:10.1021/cc8000635

    Article  PubMed  CAS  Google Scholar 

  30. NCCLS (National Committee for Clinical Laboratory Standards) (1999) Performance standards for antibacterial susceptibility testing. 9th international supplement, M100-S9 1

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Shaabani, A., Soleimani, E., Maleki, A. et al. A novel class of extended pi-conjugated systems: one-pot synthesis of bis-3-aminoimidazo[1,2-a]pyridines, pyrimidines and pyrazines. Mol Divers 13, 269–274 (2009). https://doi.org/10.1007/s11030-008-9101-0

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  • DOI: https://doi.org/10.1007/s11030-008-9101-0

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