Synthesis, Table of Contents Synthesis 2022; 54(05): 1375-1387DOI: 10.1055/s-0041-1737291 paper Divergent Synthesis of Chalcogenylated Quinolin-2-ones and Spiro[4,5]trienones via Intramolecular Cyclization of N-Arylpropynamides Mediated by Diselenides/Disulfides and PhICl2 Authors Xiaoxian Li Beibei Zhang Zhenyang Yu Dongke Zhang Haofeng Shi Lingzhi Xu Yunfei Du∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract The reaction of N-arylpropynamides with (dichloroiodo)benzene (PhICl2) and diselenides/disulfides resulted in a divergent synthesis of chalcogenylated quinolinones and spiro[4.5]trienes through intramolecular electrophilic cyclization and chalcogenylation. The chalcogenyl functional group was introduced by an electrophilic reactive organosulfenyl chloride or selenenyl chloride species, generated in situ from the reaction of disulfides/diselenides and PhICl2. Notably, the divergent cyclization pathways were determined by the substituent type on the aniline ring in N-arylpropynamide substrates. Substrates bearing a fluoro, methoxy or trifluoromethoxy group at the para-position of the aniline underwent an alternative spiralization pathway to give the 3-chalcogenylated spiro[4,5]trienones. Key words Key wordsquinolin-2-ones - diselenides/disulfides - PhICl2 - intramolecular cyclization - spiro[4,5]trienones Full Text References References 1a Park HB, Kim Y.-J, Lee JK, Lee KR, Kwon HC. Org. Lett. 2012; 14: 5002 1b D’yakonov VA, Trapeznikova OA, de Meijere A, Dzhemilev UM. Chem. Rev. 2014; 114: 5775 1c Rios R. Chem. Soc. Rev. 2012; 41: 1060 1d Gravel E, Poupon E. Nat. Prod. Rep. 2010; 27: 32 1e Li X, Huo X, Li J, She X, Pan X. Chin. J. Chem. 2009; 27: 1379 2a DeVita RJ, Hollings DD, Goulet MT, Wyvratt MJ, Fisher MH, Lo J.-L, Yang YT, Cheng K, Smith RG. Bioorg. Med. Chem. 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