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Synthesis of Highly Functionalized Isoxazolinediones from One-pot Reaction of Alkylidene Meldrum’s Acid with Alkyl Isocyanides in the Presence of Arylhydroxylamines

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Summary.

Alkyl isocyanides undergo a smooth reaction with alkylidene Meldrum’s acids in the presence of arylhydroxylamines to produce N 1-alkyl-2-(3,5-dioxo-2-aryltetrahydro-4-isoxazolyl)alkanamides in high yields.

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References

  • MP Sadashiva H Mallesha NA Hitesh KS Rangappa (2004) Bioorg Med Chem 12 6389 Occurrence Handle15556757 Occurrence Handle10.1016/j.bmc.2004.09.031 Occurrence Handle1:CAS:528:DC%2BD2cXhtVSnsr3F

    Article  PubMed  CAS  Google Scholar 

  • KR Ravi-Kumar H Mallesha MP Basappa KS Rangappa (2003) Eur J Med Chem 38 613 Occurrence Handle12832133 Occurrence Handle10.1016/S0223-5234(03)00077-1 Occurrence Handle1:CAS:528:DC%2BD3sXkvVGqs70%3D

    Article  PubMed  CAS  Google Scholar 

  • Vallance P, Bush HD, Mok BJ, Hurtado-Guerrero R, Gill H, Rossiter S, Wilden JD, Caddick S (2005) Chem Commun 5563

  • P Ding MJ Miller Y Chen P Helquist AJ Oliver O Wiest (2004) Org Lett 6 1805 Occurrence Handle15151419 Occurrence Handle10.1021/ol049473r Occurrence Handle1:CAS:528:DC%2BD2cXjs1Khtbk%3D

    Article  PubMed  CAS  Google Scholar 

  • A Rescifina MA Chiacchio A Corsaro E De Clercq D Iannazzo A Mastino A Piperno G Romeo R Romeo V Valveri (2006) J Med Chem 49 709 Occurrence Handle16420056 Occurrence Handle10.1021/jm050772b Occurrence Handle1:CAS:528:DC%2BD2MXhtlant73K

    Article  PubMed  CAS  Google Scholar 

  • A Procopio S Alcaro A De Nino L Maiuolo F Ortuso G Sindona (2005) Bioorg Med Chem Lett 15 545 Occurrence Handle15664810 Occurrence Handle10.1016/j.bmcl.2004.11.048 Occurrence Handle1:CAS:528:DC%2BD2MXnsVKmtA%3D%3D

    Article  PubMed  CAS  Google Scholar 

  • P Merino T Tejero FJ Unzurrunzaga S Franco U Chiacchio MG Saita D Iannazzo A Piperno G Romeo (2005) Tetrahedron Asymmetry 16 3865 Occurrence Handle10.1016/j.tetasy.2005.11.004 Occurrence Handle1:CAS:528:DC%2BD2MXht1Oitr7J

    Article  CAS  Google Scholar 

  • B Richichi S Cicchi U Chiacchio G Romeo A Brandi (2003) Tetrahedron 59 5231 Occurrence Handle10.1016/S0040-4020(03)00772-5 Occurrence Handle1:CAS:528:DC%2BD3sXkvFKmur4%3D

    Article  CAS  Google Scholar 

  • P Merino S Franco FL Merchan T Tejero (2000) J Org Chem 65 5575 Occurrence Handle10970296 Occurrence Handle10.1021/jo0002689 Occurrence Handle1:CAS:528:DC%2BD3cXlsVSlsbo%3D

    Article  PubMed  CAS  Google Scholar 

  • DG Piotrowska (2006) Tetrahedron 62 12306 Occurrence Handle10.1016/j.tet.2006.10.011 Occurrence Handle1:CAS:528:DC%2BD28Xht1Cmtr7P

    Article  CAS  Google Scholar 

  • A Padwa WH Pearson (2002) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products Wiley New York

    Google Scholar 

  • S Kobayashi KA Jørgensen (2001) Cycloaddition Reactions in Organic Synthesis Wiley-VCH Weinheim

    Google Scholar 

  • Yavari I, Habibi A (2004) Synthesis 989; Yavari I, Hosseini-Tabatabaei MR, Habibi A (2003) Synth Commun 33: 2709; Yavari I, Habibi A, Hosseini-Tabatabaei MR, Bijanzadeh HR (2003) Monatsh Chem 134: 1651; Yavari I, Habibi A (2003) Polish J Chem 78: 71

  • Burnett AMN, Johnson CK (1996) ‘Oak Ridge National Laboratory Report ORNL-6895’

  • Domling A (2006) Chem Rev 106: 17; Ugi I (1982) Angew Chem Intl Ed Eng 21: 810; Domling A, Ugi I (2000) Angew Chem Intl Ed Eng 39: 3168

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Habibi, A., Mousavifar, L., Yavari, I. et al. Synthesis of Highly Functionalized Isoxazolinediones from One-pot Reaction of Alkylidene Meldrum’s Acid with Alkyl Isocyanides in the Presence of Arylhydroxylamines. Monatsh. Chem. 138, 603–606 (2007). https://doi.org/10.1007/s00706-007-0630-5

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  • DOI: https://doi.org/10.1007/s00706-007-0630-5

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