Synthesis of o-Sulfinylanilines from N-Alkyl Sulfoximines and Arynes

Abstract

N-Alkyl sulfoximines react with arynes generated in situ under mild conditions providing o-sulfinylanilines in good yields. The transformation is characterized by a broad substrate scope and a good functional group tolerance. The structure of a reaction product was confirmed by single-crystal X-ray diffraction.Note pubs.acs.org/joc

Cascade Nucleophilic Addition–Cyclic Michael Addition of Arynes and Indoles Bearing Michael Acceptor: A Strategy to Construct Pyrroloacridines and Study of Their Physicochemical Properties

“…Kobayashi and co-workers developed an efficient method for o -(trimethylsilyl)­phenyl triflate as a benzyne precursor in 1983 . However, people witnessed a flourishing advance in aryne chemistry, which was mainly attributed to the exponential applications of Kobayashi’s method in the past 20 years . In connection with our ongoing research interest in developing novel and efficient methodologies by using aryne intermediates, we were attracted to utilizing substituted indoles having a suitable Michael acceptor to form a six-membered ring after the reaction with aryne.…”

“…These cascade procedures not only possess the atom- and step-economy products but also could quickly build up the complexity of the challenging structural motifs. Several heterocyclic compounds were prepared by utilizing a cascade nucleophilic addition–electrophilic cyclizing reaction of Nu-E bifunctional reactants with arynes. , In particular, the synthesis of distinctly substituted indolines and isoquinolines by the coupling reaction of N -acyl dehydroamino esters with arynes was initially discovered by Stolz et al in 2008 (Scheme ). Later in 2010, Huang and co-workers used anilines containing an α,β-unsaturated ketone moiety on the ortho position with arynes and obtained nine-functionalized acridines .…”

“…Next, the experiments were conducted carefully at higher temperatures (Table , entries 8–9), where we found a reasonable improvement of the yield at 60 °C in THF (Table , entry 10). We planned to use some of the additives, such as 18-crown-6 and 4 Å MS, as they provided better results quite often . The usage of individual additives 18-crown-6 and 4 Å MS gave promising results in terms of yield of product 3a (Table , entries 11 and 12).…”