Synthesis, Table of Contents Synthesis 2020; 52(04): 544-552DOI: 10.1055/s-0039-1690244 paper © Georg Thieme Verlag Stuttgart · New York Copper-Catalyzed Aerobic Oxidative Alkynylation of 3,4-Dihydroquinoxalin-2-ones Jaume Rostoll-Berenguer , Gonzalo Blay , José R. Pedro∗ , Carlos Vila ∗ Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain Email: jose.r.pedro@uv.es Email: carlos.vila@uv.es › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry Abstract Herein, we described a ligand-free copper-catalyzed aerobic oxidative functionalization of 3,4-dihydroquinoxalin-2(1H)-ones with terminal alkynes using visible-light and oxygen as terminal oxidant to give 3-ethynyl-3,4-dihydroquinoxalin-2(1H)-one, cyclic propargylic amines, in moderate to good yields. Moreover, we demonstrate the versatility of the 3-ethynyl-3,4-dihydroquinoxalin-2(1H)-ones obtained by preparing several 3,4-dihydroquinoxalin-2-one derivatives. Key words Key wordsdihydroquinoxalinones - alkynes - copper - cross-dehydrogenative coupling - oxidation - nitrogen heterocycles Full Text References References 1a Li C.-J. Acc. Chem. Res. 2009; 42: 335 1b Scheuermann CJ. Chem. Asian J. 2010; 5: 436 1c Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215 1d Zhang S.-Y, Zhang F.-M, Tu Y.-Q. Chem. Soc. Rev. 2011; 40: 1937 1e Girard CR, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74 1f Yang L, Huang H.-M. Chem. Rev. 2015; 115: 3468 2a Li C.-J, Li Z.-P. Pure Appl. Chem. 2006; 78: 935 2b Li Z.-P, Bohle D.-S, Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 8928 2c Beatty JW, Stephenson CR. Acc. Chem. Res. 2015; 48: 1474 3 Lauder K, Toscani A, Scalacci N, Castagnolo D. Chem. Rev. 2017; 117: 14091 4a Yu PH, Davis BA, Boulton AA. J. Med. 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Chem. 2013; 56: 9275 20 Although we observed in all reactions full conversion of quinoxalin-2-ones 1, the corresponding alkynylated product 3 was accompanied with other byproducts: the oxidation of 1 to the corresponding hemiaminal and the corresponding 1,4-dihydroquinoxaline-2,3-dione. Supplementary Material Supplementary Material Supporting Information
