Intramolecular Michael and Anti-Michael Additions to Carbon-Carbon Triple Bonds

Intramolecular nucleophilic addition reactions to carbon-carbon triple bonds have considerable synthetic potential for the preparation of a variety of organic compounds. This account describes the synthesis of heterocyclic compounds by both Michael and anti-Michael addition reactions to the triple bonds in alkyl phenylethynyl ketones and ynamides via the dithiocarboxylation, thiocarboxylation or thiocarbamoylation of the acidic CH or NH groups in these molecules. 1. Introduction 2. Dithiocarboxylation of Alkyl Phenylethynyl Ketones 3. Reactions of Ynamides with Heterocumulenes 4. Reactions of Derivatives of Phenylpropynoic Acid Bearing a Heteroatom-Acceptor-Substituted Methylene Group 4.1 Intramolecular Michael Addition of Carbanions to Carbon-Carbon Triple Bonds 4.2 2H-1,4-Thiazin-3(4H)-ones by Thiocarbamoylation of N,N-Disubstituted Phenylpropynamides 5. Conclusion