Benzannulation and <i>N</i>‐Annulation of β‐Ketoenamines for Synthesizing Aniline and Pyridine Derivatives Using DMSO as a Methine Source
Pallaba Ganjan Dalai, Niranjan Panda
Abstract
Abstract Benzannulation and N ‐annulation of β‐ketoenamines by the in‐situ generated methyl(methylene)sulfonium ion from the reaction of dimethyl sulfoxide (DMSO) and 1,2‐dibromoethane (DBE) was achieved. The β‐ketoenamines underwent N‐annulation to pyridine derivatives, while the N ‐alkylated enamines were benzannulated to afford substituted anilines. The utility of the intermediate methyl(methylene)sulfonium ion was further extended for synthesizing methylene‐bridged bis‐1,3‐dicarbonyl compounds. magnified image
Topics & Concepts
ChemistryAnnulationSulfoniumMethyleneAnilinePyridineAlkylationMedicinal chemistryOrganic chemistryCatalysisSalt (chemistry)Catalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques