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Short Communication

Three-component reaction of isocyanide with dialkyl acetylenedicarboxylate and alkyl mercaptan: preparation of new derivatives of stable ketenimines

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Pages 117-123 | Received 18 Sep 2014, Accepted 15 Oct 2014, Published online: 17 Nov 2014

References

  • Frausto da Silva JR, Williams RJP. The biological chemistry of the elements. New York, NY: Oxford University Press; 2001.
  • Clayden J, MacLellan P. Asymmetric synthesis of tertiary thiols and thioethers Beilstein. J Org Chem. 2011;7:582–595.
  • Chauhan P, Mahajan S, Enders D. Organocatalytic carbon−sulfur bond-forming reactions. Chem Rev. 2014;114:8807–8864. doi: 10.1021/cr500235v
  • Alajarin M, Vidal A, Tovar F. An intramolecular ketenimine–ketenimine [4+2] cycloaddition reaction. Targets Heterocycl Syst. 2000;3:4293–4326.
  • Sung K, Huang PM, Chiang SM. Kinetic studies for amination of ketenimines: change of rate-determining step by electron-withdrawing N-substituents through electronic effects. Tetrahedron. 2006;62:4795–4799. doi: 10.1016/j.tet.2006.03.022
  • Alajarin M, Marin-Luna M, Vidal A. Recent highlights in ketenimine chemistry. Eur J Org Chem. 2012;2012:5637–5653. doi: 10.1002/ejoc.201200383
  • Krow GR. Synthesis and reactions of ketenimines. Angew Chem Int Ed. 1971;27:435–449. doi: 10.1002/anie.197104351
  • Shaabani A, Maleki A, Rezayan AH, Sarvary A. Recent progress of isocyanide-based multicomponent reactions in Iran. Mol Diversity. 2011;15:41–68. doi: 10.1007/s11030-010-9258-1
  • Shaabani A, Sarvary A, Maleki A. Zwitterions and zwitterion-trapping agents in isocyanide chemistry. In: Nenajdenko VG, editor. Isocyanide chemistry: applications in synthesis and material science. Weinheim: Wiley-VCH Verlag GmbH. Available from http://onlinelibrary.wiley.com/doi/10.1002/9783527652532.ch8/summary
  • Shaabani A, Sarvary A, Ghasemi S, Rezayan AH, Ghadari R, Ng SW. An environmentally benign approach for the synthesis of bifunctional sulfonamide-amide compounds via isocyanide-based multicomponent reactions. Green Chem. 2011;13:582–585. doi: 10.1039/c0gc00442a
  • Alizadeh A, Rostamnia S. Facile synthesis of highly functionalized stable ketenimines via a three-component reaction. Synthesis. 2008;1:57–60. doi: 10.1055/s-2007-990894
  • Sarvary A, Shaabani S, Shaabani A, Ng SW. A two-step synthesis of 1,5-disubstituted tetrazoles containing a siloxy or sulfonamide group. Tetrahedron Lett. 2011;52:5930–5933. doi: 10.1016/j.tetlet.2011.08.114
  • Oae S, Kiritani R. The nucleophilic replacement of the phenolic hydroxy group by the mercapto group in acidic media. Bull Chem Soc Japan. 1965;38:1381–1385. doi: 10.1246/bcsj.38.1381
  • Meindertsma AF, Pollard MM, Feringa BL, de Vriesa JG, Minnaard AJ. Asymmetric hydrogenation of alkyl(vinyl)thioethers: a promising approach to a-chiral thioethers. Tetrahedron Asymmetr. 2007;18:2849–2858. doi: 10.1016/j.tetasy.2007.11.020

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