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Synthesis of quinolin-2-ones from ortho-vinylcarbonylamino-substituted acylbenzenes by tandem Michael and Knoevenagel reactions

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Chemistry of Heterocyclic Compounds Aims and scope

Consecutive Michael addition and Knoevenagel intramolecular condensation reactions provide 3-alkoxymethyl-, 3-aminomethyl-, and 3-benzylquinolin-2-ones from o-(vinylcarbonylamino)acyl-benzenes. The synthesis of 3-alkoxymethylquinolin-2-ones may be carried out in a one-pot procedure directly from o-(vinylcarbonylamino)acylbenzenes. Aminomethylquinolin-2-ones are formed in one-pot approach only from corresponding o-(vinylcarbonylamino)benzophenones. Their analogs with o-alkyl-carbonyl groups form Michael adducts under these conditions.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 1, Build. 3, Leninskie Gory, Moscow, 119992, Russia

    S. S. Mochalov, A. N. Fedotov, E. V. Trofimova & N. S. Zefirov

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  1. S. S. Mochalov
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  2. A. N. Fedotov
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  3. E. V. Trofimova
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  4. N. S. Zefirov
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Correspondence to S. S. Mochalov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1583-1598, October, 2013.

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Mochalov, S.S., Fedotov, A.N., Trofimova, E.V. et al. Synthesis of quinolin-2-ones from ortho-vinylcarbonylamino-substituted acylbenzenes by tandem Michael and Knoevenagel reactions. Chem Heterocycl Comp 49, 1469–1483 (2014). https://doi.org/10.1007/s10593-014-1398-2

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  • DOI: https://doi.org/10.1007/s10593-014-1398-2

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