SYNTHESIS OF QUINOLIN-2-ONES FROM <i>ortho</i>-VINYLCARBONYLAMINO-SUBSTITUTED ACYLBENZENES BY TANDEM MICHAEL AND KNOEVENAGEL REACTIONS

Authors

  • C. C. Мочалов M. V. Lomonosov Moscow State University
  • А. Н. Федотов M. V. Lomonosov Moscow State University
  • Е. В. Трофимова M. V. Lomonosov Moscow State University
  • Н. С. Зефиров M. V. Lomonosov Moscow State University

DOI:

https://doi.org/10.1007/747

Keywords:

N-(2-acylphenyl)prop-2-enamides, N-(7-acyl-2, 3-dihydro-1, 4-benzodioxin-6-yl)prop-2-enamides, quinolin-2-ones, intramolecular Knoevenagel reaction

Abstract

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-alkylcarbonyl groups form Michael adducts under these conditions.

How to Cite
Mochalov, S. S.; Fedotov, A. N.; Trofimova, E. V.; Zefirov, N. S. Chem. Heterocycl. Compd. 2014, 49, 1464. [Khim. Geterotsikl. Soedin. 2013, 1583.]

For this article in the English edition see DOI 10.1007/s10593-014-1398-2

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Published

2013-10-22

Issue

No. 10 (2013)

Section

Original Papers