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An experimental NMR and computational study of 4-quinolones and related compounds

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Abstract

We report the synthesis and structural study of eight compounds, either quinolin-4(1H)-ones or quinolines. Tautomerism as well as (E) → (Z) and rotational isomerism were studied both experimentally (1H and 13C NMR) and theoretically [B3LYP/6-311++G(d,p)].

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Acknowledgments

Thanks are due to the University of Aveiro, FCT, and FEDER for funding the Organic Chemistry Research Unit, the Project POCI/QUI/58835/2004 and the Portuguese National NMR Network (RNRMN). R.S.G.R.S. also thanks FCT for her PhD Grant (SFRH/BD/30734/2006). We thank the Ministerio de Ciencia e Innovación (project no. CTQ2009-13129-C02-02), the Spanish MEC (CTQ2007-62113), and the Comunidad Autónoma de Madrid (project MADRISOLAR2, ref. S2009/PPQ-1533) for continuing support. Thanks are given to the CTI (CSIC) for an allocation of computer time.

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Authors and Affiliations

  1. Chemistry Department and QOPNA, University of Aveiro, 3810-193, Aveiro, Portugal

    Raquel S. G. R. Seixas & Artur M. S. Silva

  2. Instituto de Química Médica, CSIC, Juan de la Cierva 3, 28006, Madrid, Spain

    Ibon Alkorta & José Elguero

Authors
  1. Raquel S. G. R. Seixas
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  2. Artur M. S. Silva
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  3. Ibon Alkorta
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  4. José Elguero
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Correspondence to Artur M. S. Silva.

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Seixas, R.S.G.R., Silva, A.M.S., Alkorta, I. et al. An experimental NMR and computational study of 4-quinolones and related compounds. Monatsh Chem 142, 731–742 (2011). https://doi.org/10.1007/s00706-011-0473-y

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  • DOI: https://doi.org/10.1007/s00706-011-0473-y

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