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\(N,N,N^{\prime },N^{\prime }\)-Tetrabromobenzene-1,3-disulfonamide and poly(\(N\)-bromo-\(N\)-ethylbenzene-1,3-disulfonamide) as new and efficient catalysts for the synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives

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Abstract

Various mono and bis-1,6-dihydropyrazine-2,3-dicarbonitrile derivatives were efficiently synthesized by reacting 2,3-diaminomaleonitrile (DAMN), isocyanides and ketones in the presence of a catalytic amount of \(N,N{,}N^{\prime }{,}N^{\prime }\)-tetrabromobenzene-1,3-disulfonamide [TBBDA] and poly(\(N\)-bromo-\(N\)-ethylbenzene-1,3-disulfonamide) [PBBS] in EtOH/H\(_{2}\)O at ambient temperature.

Graphic abstract \(N,N,N^{\prime },N^{\prime }\) -Tetrabromobenzene-1,3-disulfonamide and poly( \(N\)-bromo-\(N\)-ethylbenzene-1,3-disulfonamide) as new and efficient catalysts for the synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives.

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References

  1. Ohkanda J, Katoh A (1998) $N$-hydroxyamide-containing heterocycles-synthesis, reactivities, and iron (III) chelating properties. Rev Heteroatom Chem 18:87–118

    Google Scholar 

  2. Dell A, William DH, Morris HR, Smith GA, Feeney J, Roberts GCK (1975) Structure revision of the antibiotic echinomycin. J Am Chem Soc 97:2497–2502. doi:10.1021/ja00842a029

    Article  PubMed  CAS  Google Scholar 

  3. Bailly C, Echepare S, Gago F, Waring MJ (1999) Recognition elements that determine affinity and sequence-specific binding to DNA of 2QN, a biosynthetic bis-quinoline analogue of echinomycin. Anti Cancer Drug Des 14:291–303

    CAS  Google Scholar 

  4. Habibi A, Shikhhosseini-Lori E, Shockravi A (2009) Synthesis of novel furo-pyran derivatives via reaction between an isocyanide and alkylidene substituted Meldrum’s acid. Tetrahedron Lett 50:1075–1078. doi:10.1016/j.tetlet.2008.12.082

    Google Scholar 

  5. Domling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168–3210. doi:10.1002/15213773(20000915)39:18%3c3168

    Google Scholar 

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

    Article  PubMed  Google Scholar 

  7. Yamaguchi T, Matsumoto S, Watanabe K (1998) Generation of free radicals from Dihydropyrazines with DNA strand-breakage activity. Tetrahedron Lett 39: 8311–8312. doi:10.1016/S0040-4039(98)01859-0

    Google Scholar 

  8. Takeda O, Takechi S, Katoh T, Yamaguchi T (2005) Effects of phenyl derivatives of dihydropyrazines with ability to generate radical species on Escherichia coli. Biol Pharm Bull 28:1161–1164. doi:10.1248/bpb.30.1663

    Article  PubMed  CAS  Google Scholar 

  9. Singh SK, Saibaba V, Ravikumar V, Rudrawar SV, Daga P, Rao CS, Akhila V, Hegde P, Rao YK (2004) Synthesis and biologicalevaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors. Bioorg Med Chem 12:1881–1893. doi:10.1016/j.bmc.2004.01.033

    Article  PubMed  CAS  Google Scholar 

  10. Brown DJ (2004) Quinoxalines supplements II. In: Taylor EC, Wipf P (eds) chemistry of heterocyclic compounds. Wiley, Hoboken

    Google Scholar 

  11. Bhosale RS, Sarda SR, Andhapure SS, Jadhav WN, Bhusare SR, Pawar RP (2005) An efficient protocol for the synthesis of quinoxalinederivatives at room temperature using molecular iodine as thecatalyst. Tetrahedron Lett 46:7183–7186. doi:10.1016/j.tetlet.2005.08.080

    Article  CAS  Google Scholar 

  12. More SV, Sastry MNV, Yao C-F (2006) Cerium (IV) ammonium nitrate (CAN) as a catalyst in tap water: a simple, proficient and green approach for the synthesis of quinoxalines. Green Chem 8:91–95. doi:10.1039/B510677J

    Article  CAS  Google Scholar 

  13. Aparicio D, Attanasi OA, Filippone P, Ignacio R, Lillini S, Mantellini F, Palacios F, de los Santos JM (2006) Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions. J Org Chem 71:5897–5905. doi:10.1021/jo060450v

    Google Scholar 

  14. Zhang X, Sui Z (2006) Application of carbenoid N-Hinsertion in the synthesis of the tricyclic 1,4-dihydropyrazines. Tetrahedron Lett 47:5953–5955. doi:10.1016/j.tetlet.2006.06.053

    Article  CAS  Google Scholar 

  15. Dubinina GG, Platonov MO, Golovach SM, Borysco PO, Tolmachov AO, Volovenko YM (2006) Novel 5,7-disubstituted 6-amino-5H-pyrrolo[3,2-b]pyrazine-2,3- dicarbonitriles, the promising protein kinase inhibitors with antiproliferative activity. Eur J Med Chem 41:727–737. doi:10.1016/j.ejmech.2006.03.019

    Google Scholar 

  16. Li J, Liu Y, Li C, Jia X (2009) CAN-catalyzed syntheses of 3,4-dihydroquinoxalin-2-amine derivatives based on isocyanides. Tetrahedron Lett 50:6502–6505. doi:10.1016/j.tetlet.2009.09.022

    Google Scholar 

  17. Fujiwara S-I, Asanuma Y, Shin-ike T, Kambe N (2007) Copper(I)-catalyzed highly efficient synthesis of benzoselenazoles and benzotellurazoles. J Org Chem 12:8087–8090. doi:10.1021/jo7013164 (ISSN: 0022-3263)

    Google Scholar 

  18. Ugi I, Domling A, Werner B (2000) Since 1995 the new chemistry of multicomponent reactions and their libraries, including their heterocyclic chemistry. J Heterocycl Chem 37:647–658. doi:10.1002/jhet.5570370322

    Article  CAS  Google Scholar 

  19. Krasavin M, Parchinsky V (2008) Expedient Entry into 1,4- dihydroquinoxalines and quinoxalines via a novel variant of isocyanide-based MCR. Synlett 5:645–648. doi:10.1055/s-2008-1032106

    Article  Google Scholar 

  20. Krasavin M, Shkavrov S, Parchinsky V, Bukhryakov K (2009) Imidazo[1,2-a]quinoxalines accessed via two sequential isocyanide-based multicomponent reactions. J Org Chem 74: 2627–2629. doi:10.1021/jo900050k

    Google Scholar 

  21. Nikulnikov M, Tsirulnikov S, Kysil V, Ivachtchenko A, Krasavin M (2009) tert-Butyl isocyanide as convertible reagent in Ugi reaction: Microwave-assisted preparation of 5,6-dihydropyrazolo[1,5-a]pyrazine-4,7-diones. Synlett 2:260–262. doi:10.1002/chin.200922162

    Google Scholar 

  22. Krasavin M, Tsirulnikov S, Nikulnikov M, Kysil V, Ivachtchenko A (2008) Poorly reactive 5-piperazin-1-yl-1,3,4-thiadiazol-2-amines rendered as valid substrates for Groebke-Blackburn type multi-component reaction with aldehydes and isocyanides using TMSCl as a promoter. Tetrahedron Lett 49:5241–5243. doi:10.1016/j.tetlet.2008.06.113

    Article  CAS  Google Scholar 

  23. Kysil V, Tkachenko S, Khvat A, Williams C, Tsirulnikov S, Churakova M, Ivachtchenko A (2007) TMSCl-promoted isocyanide-based MCR of ethylenediamines: an efficient assembling of 2-aminopyrazine core. Tetrahedron Lett 48(36):6239–6244. doi:10.1016/j.tetlet.2007.07.044

    Google Scholar 

  24. Ghorbani-Vaghei R, Jalili H (2005) Mild and regioselective bromination of aromatic compounds with $N, N, N^{\prime }, N^{\prime }$-tetrabromobenzene- 1,3-disulfonylamide and poly($N$- bromobenzene-1,3- disulfonylamide). Synthesis 7:1099–1102. doi:10.1055/s-2005-861851

    Google Scholar 

  25. Ghorbani-Vaghei R, Shahbazee E, Veisi H (2005) $N, N^{\prime }$-Diiodo-$N, N^{\prime }$-1,2-ethanediy toluenesulfonamide) as a reagent for conversion of aldehydes to methyl esters. Mendeleev Commun 15:207–208. doi:10.1070/MC2005v015n05ABEH002091

    Article  Google Scholar 

  26. Ghorbani-Vaghei R, Zolfigol MA, Chegeny M, Veisi H (2006) Poly($N$-bromobenzene- 1,3-disulfonamide) and $N, N, N^{\prime }, N^{\prime }$-tetrabromobenzene-1,3-disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, and thiols using hexamethyldisilazane. Tetrahedron Lett 47:4505–4508. doi:10.1016/j.tetlet.2006.03.157

    Article  CAS  Google Scholar 

  27. Ghorbani-Vaghei R, Shahbazee E (2005) Facile and mild deprotection of semicarbazones under solvent-free conditions with $N, N, N^{\prime }, N^{\prime }$-tetrabromo-benzene-1,3-disulfonylamide. J Braz Chem Soc 16:647–649

    Article  CAS  Google Scholar 

  28. Zolfigol MA, Ghorbani-Vaghei R, Mallakpour S, Chehardoli G, Ghorbani Choghamani A, Yazdi Hosain A (2006) Simple, convenient and heterogeneous method for conversion of urazoles to triazolinediones using $N, N, N^{\prime }, N^{\prime }$-tetrabromobenzene-1,3-disulfonylamide or trichloromelamine under mild and heterogeneous conditions. Synthesis 10:1631–1634. doi:10.1055/s-2006-926446

    Google Scholar 

  29. Ghorbani-Vaghei R, Akbari-Dadamahaleh S (2009) Poly($N$-bromo-$N$-ethylbenzene-1,3 disulfonamide) and $N, N, N^{\prime }, N^{\prime }$-tetrabromobenzene-1,3-disulfonamide as efficient reagents for synthesis of quinolines. Tetrahedron Lett 50:1055–1058. doi:10.1016/j.tetlet.2008.12.076

    Article  CAS  Google Scholar 

  30. Ghorbani-Vaghei R (2003) Mild and regioselective iodination of aromatic compounds with $N, N^{\prime }$-diiodo-$N, N^{\prime }$-1,2-ethanediyl bis ($p$-toluenesulphonamide). Tetrahedron Lett 44:7529–7532. doi:10.1016/j.tetlet.2003.08.019

  31. Ghorbani-Vaghei R, Chegini M, Veisi H, Karimi-Tabar M (2009) Poly($N, N^{\prime }$-dibromo- $N$-ethyl-benzene-1,3-disulfonamide) $N, N, N^{\prime }, N^{\prime }$-tetrabromobenzene-1,3 disulfonamide and novel poly($N, N^{\prime }$-dibromo-$N$-phenylbenzene-1,3-disulfonamide) as powerful reagents for benzylic bromination. Tetrahedron Lett 50:1861–1865. doi:10.1016/j.tetlet.2009.02.007

    Google Scholar 

  32. Ghorbani-Vaghei R, Veisi H, Keypour H, Dehghani-Firouzabadi A (2010) A practical and efficient synthesis of bis(indolyl) methanes in water, and synthesis of di-, tri- and tetra(bis- indolyl)methanes under thermal conditions catalyzed by oxalic acid dihydrate. Mol Divers 14:87–96. doi:10.1007/s11030-009-9150-z

    Google Scholar 

  33. Ghorbani-Vaghei R, Toghraei-Semiromi Z, Karimi-Nami R (2011) One-pot synthesis of 4H-chromene and dihydropyrano[3,2-c]chromene derivatives in hydroalcoholic media. J Braz Chem Soc 22:905–909

    CAS  Google Scholar 

  34. Ghorbani-Vaghei R, Karimi-Nami R, Toghraei-Semiromi Z, Amiri M, Ghavidel M (2011) One-pot synthesis of aliphatic and aromatic 2H-indazolo[2,1-b]phthalazine-triones catalyzed by $N$-halosulfonamides under solvent-free conditions. Tetrahedron 67:1930–1937. doi:10.1016/j.tet.2011.01.024

    Google Scholar 

  35. Ghorbani-Vaghei R, Shahbazi H, Veisi H (2012) Mild bromination of unreactive aromatic compounds. Tetrahedron Lett 53: 2325–2327. doi:10.1016/j.tetlet.2012.02.101

    Google Scholar 

  36. Ghorbani-Vaghei R, Veisi H (2010) The application of poly($N, N^{\prime }$-dibromo-$N$-ethyl- benzene-1,3-disulfonamide) and N, N, N’, N’-tetrabromobenzene-1,3-disulfonamide as catalysts for one-pot synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles and 1,5- benzodiazepines, and new reagents for synthesis of benzimidazoles. Mol Divers 14:249–256. doi:10.1007/s11030-009-9169-1

    Google Scholar 

  37. Veisi H, Ghorbani-Vaghei R (2010) Recent progress in the application of $N$-halo reagents in the synthesis of heterocyclic compounds. Tetrahedron 66:7445–7463. doi:10.1016/j.tet.2010.07.015

    Article  CAS  Google Scholar 

  38. Grieco PA (1998) Organic synthesis in water. Blackie Academic and Professional, London

    Book  Google Scholar 

  39. Li C-J (2005) Organic reactions in aqueous media with a focus on C-C bond formations: a decade update. Chem Rev 105:3095–3165. doi:10.1021/cr030009u

    Google Scholar 

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Acknowledgments

We are thankful to Bu-Ali Sina University, Center of Excellence in development of environmentally friendly methods for chemical synthesis (CEDEFMCS) for financial support.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali-Sina University, 65174 , Hamedan, Iran

    Ramin Ghorbani-Vaghei, Mostafa Amiri, Rahman Karimi-Nami & Zahra Toghraei-Semiromi

  2. Department of Chemistry, Faculty of Science, Urmia University, 57154 , Urmia, Iran

    Mehdi Ghavidel

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  1. Ramin Ghorbani-Vaghei
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Correspondence to Ramin Ghorbani-Vaghei.

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Ghorbani-Vaghei, R., Amiri, M., Karimi-Nami, R. et al. \(N,N,N^{\prime },N^{\prime }\)-Tetrabromobenzene-1,3-disulfonamide and poly(\(N\)-bromo-\(N\)-ethylbenzene-1,3-disulfonamide) as new and efficient catalysts for the synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives. Mol Divers 17, 251–259 (2013). https://doi.org/10.1007/s11030-013-9427-0

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