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Multicomponent synthesis of benzoxazinones via tandem Ugi/Mitsunobu reactions: an unexpected cine-substitution

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Abstract

A short (2 steps) synthesis of diverse benzoxazinones by coupling the Ugi multicomponent reaction with an intramolecular Mitsunobu substitution is reported. The cyclization step proceeds via an unexpected cine substitution.

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References

  1. Domling 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 

  2. Banfi L, Riva R (2005) The Passerini reaction. Org React 65: 1–140

    CAS  Google Scholar 

  3. Marcaccini S, Torroba T (2007) The use of the Ugi four-component condensation. Nat Protocols 2: 632–639 doi:10.1038/nprot.2007.71

    Article  CAS  Google Scholar 

  4. Hulme C, Nixey T (2003) Rapid assembly of molecular diversity via exploitation of isocyanide-based multi-component reactions. Curr Opin Drug Discov Dev 6: 921–929

    CAS  Google Scholar 

  5. Marcaccini S, Torroba T (2005) Post-condensation transformations of the Passerini and Ugi reactions. In: Zhu J, Bienaymé H(eds) Multicomponent reactions. Weinheim, Wiley-VCH, pp 1–32

    Google Scholar 

  6. Akritopoulou-Zanze I, Djuric SW (2007) Recent advances in the development and applications of post-Ugi transformations. Heterocycles 73: 125–147

    Article  CAS  Google Scholar 

  7. Zhu JP (2003) Recent developments in the isonitrile-based multicomponent synthesis of heterocycles. Eur J Org Chem 1133–1144. doi:10.1002/ejoc.200390167

  8. Banfi L, Basso A, Guanti G, Kielland N, Repetto C et al (2007) Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives. J Org Chem 72: 2151–2160 doi:10.1021/jo062626z

    Article  PubMed  CAS  Google Scholar 

  9. Banfi L, Basso A, Guanti G, Lecinska P, Riva R (2006) Multicomponent synthesis of dihydrobenzoxazepinones by coupling Ugi and Mitsunobu reactions. Org Biomol Chem 4: 4236–4240 doi:10.1039/b613056a

    Article  PubMed  CAS  Google Scholar 

  10. Banfi L, Basso A, Guanti G, Lecinska P, Riva R et al (2007) Multicomponent synthesis of novel 2-and 3-substituted dirydrobenzo[1,4]oxazepinones and tetrahydrobenzo[1,4]diazepin-5-ones and their conformational analysis. Heterocycles 73: 699–728

    CAS  Google Scholar 

  11. Kim YB, Choi EH, Keum G, Kang SB, Lee DH et al (2001) An efficient synthesis of morpholin-2-one derivatives using glycolaldehyde dimer by the Ugi multicomponent reaction. Org Lett 3: 4149–4152 doi:10.1021/ol016716w

    Article  PubMed  CAS  Google Scholar 

  12. Miller MJ, Mattingly PG, Morrison MA, Kerwin JF Jr (1980) Synthesis of β-lactams from substituted hydroxamic acids. J Am Chem Soc 102: 7026–7032 doi:10.1021/ja00543a021

    Article  CAS  Google Scholar 

  13. Yamato M, Hashigaki K, Tsutsumi A, Tasaka K (1981) Synthesis and structure-activity relationship of spiro[isochroman-piperidine] analogs for inhibition of histamine release. II. Chem Pharm Bull (Tokyo) 29: 3494–3498

    CAS  Google Scholar 

  14. Rieu JP, Duflos A, Tristani JC, Patoiseau JF, et al (1993) Synthesis and bradycardiac activity of a series of substituted 3-aminoalkyl-2,3-dihydro-4H-1,3-benzoxazin-4-ones as potent antiischemics. Eur J Med Chem 28: 683–691 doi:10.1016/0223-5234(93)90027-C

    Article  CAS  Google Scholar 

  15. Norman MH, Kelley JL, Hollingsworth EB (1993) Conformationally restricted analogues of remoxipride as potential antipsychotic agents. J Med Chem 36: 3417–3423 doi:10.1021/jm00074a023

    Article  PubMed  CAS  Google Scholar 

  16. Benedini F, Bertolini G, Cereda R, Dona G, Gromo G et al (1995) New antianginal nitro esters with reduced hypotensive activity—synthesis and pharmacological evaluation of 3-[(nitrooxy)alkyl]-2H-1,3-benzoxazin-4(3H)-ones. J Med Chem 38: 130–136 doi:10.1021/jm00001a018

    Article  PubMed  CAS  Google Scholar 

  17. Minghetti P, Casiraghi A, Cilurzo F, Montanari L, Monzani MV et al (2000) Solvation enthalpies as descriptors of structure-in vitro percutaneous permeation relationship of benzoxazinones regioisomers. Farmaco 55: 563–568 doi:10.1016/S0014-827X(00)00048-3

    Article  PubMed  CAS  Google Scholar 

  18. Wellington KD, Cambie RC, Rutledge PS, Bergquist PR (2000) Chemistry of sponges. 19. Novel bioactive metabolites from Hamigera tarangaensis. J Nat Prod 63: 79–85 doi:10.1021/np9903494

    Article  PubMed  CAS  Google Scholar 

  19. Madhavan GR, Chakrabarti R, Reddy KA, Rajesh BM, Balraju V et al (2006) Dual PPAR-α and -γ-activators derived from novel benzoxazinone containing thiazolidinediones having antidiabetic and hypolipidemic potential. Bioorg Med Chem 14: 584–591 doi:10.1016/j.bmc.2005.08.043

    Article  PubMed  CAS  Google Scholar 

  20. Kamei K, Maeda N, Nomura K, Shibata M, et al (2006) Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: discovery of piclozotan. Bioorg Med Chem 14: 1978–1992 doi:10.1016/j.bmc.2005.10.046

    Article  PubMed  CAS  Google Scholar 

  21. Heindel ND, Schaeffer LA (1970) A new class of 1,3-benzoazinones as potential central nervous system agents. J Med Chem 13: 981–983 doi:10.1021/jm00299a047

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146, Genova, Italy

    Luca Banfi, Andrea Basso, Giuseppe Guanti, Paulina Lecinska & Renata Riva

Authors
  1. Luca Banfi
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  2. Andrea Basso
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  3. Giuseppe Guanti
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  4. Paulina Lecinska
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  5. Renata Riva
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Correspondence to Luca Banfi.

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Banfi, L., Basso, A., Guanti, G. et al. Multicomponent synthesis of benzoxazinones via tandem Ugi/Mitsunobu reactions: an unexpected cine-substitution. Mol Divers 12, 187–190 (2008). https://doi.org/10.1007/s11030-008-9087-7

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  • DOI: https://doi.org/10.1007/s11030-008-9087-7

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