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

C. C. Мочалов, А. Н. Федотов, Е. В. Трофимова, Н. С. Зефиров
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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


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

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