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

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.