Synlett, Table of Contents Synlett 2023; 34(08): 970-974DOI: 10.1055/a-1996-2853 letter Denitrosation of Aryl-N-nitrosamines by a Transnitrosation Strategy Using Ethanethiol and p-Toluenesulfonic Acid under Mild Reaction Conditions Vimlesh Kumar Kanaujiya a Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, 221005, India , Varsha Tiwari a Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, 221005, India , Siddharth Baranwal a Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, 221005, India , Vandana Srivastava a Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, 221005, India , Jeyakumar Kandasamy ∗ a Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, 221005, India b Department of Chemistry, Pondicherry University, Pondicherry, 605014, India› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract A convenient and practical route is reported for the denitrosation of aryl-N-nitrosamines under mild reaction conditions using ethanethiol and PTSA. The reactions proceeds at room temperature and the amines are obtained in good to excellent yields. Many functional groups that are susceptible to reduction were stable during the denitrosation. A broad substrate scope and easy operations are salient features of this method. Key words Key wordsamines - nitrosamines - denitrosation - metal-free reaction - ethanethiol - transnitrosation Full Text References References and Notes 1 Current address: Department of Chemistry, Mahant Darshan Das Mahila Mahavidyalaya, Muzaffarpur, Bihar-842002, India. 2 Current address: Department of Chemistry, Kashi Naresh Govt. PG College, Bhadohi, Uttar Pradesh, 221304, India. 3a Anselme J.-P. In N-Nitrosamines, Chap. 1. Anselme J.-P. ACS Symposium Series 101; American Chemical Society; Washington DC: 1979: 1 3b Nitrosamines and Related N-Nitroso Compounds . Loeppky RN, Michejda CJ. 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Chem. 2018; 16: 8280 15 N-Benzylaniline (2a); Typical Procedure N-Benzyl-N-nitrosoaniline (1a; 1.0 mmol, 1.0 equiv) was stirred in DCM (3 mL) for 5 min at room temperature, then PTSA (0.3 equiv) and ethanethiol (2.0 equiv) were added, and the mixture was stirred until the reaction as complete (TLC). The mixture was then diluted with DCM and washed with H2O. The organic layer was dried (Na2SO4), concentrated, and purified by column chromatography [silica gel, hexane–EtOAc (92:8)] to give a pale-yellow viscous liquid; yield: 164 mg (89%); Rf = 0.62.1H NMR (500 MHz, CDCl3): δ = 7.26–7.19 (m, 4 H), 7.18–7.13 (m, 1 H), 7.08–7.04 (m, 2 H), 6.61 (td, J = 7.4, 1.0 Hz, 1 H), 6.50 (dd, J = 8.6, 0.9 Hz, 2 H), 4.18 (s, 2 H), 3.85 (s, 1 H). 13C NMR (125 MHz, CDCl3): δ = 148.0, 139.3, 129.1, 128.5, 127.4, 127.1, 117.4, 112.7, 48.1. 16 Inami K, Kondo S, Ono Y, Saso C, Mochizuki M. Bioorg. Med. Chem. 2013; 21: 7853 17 Yi S.-L, Li M.-C, Hu X.-Q, Mo W.-M, Shen Z.-L. Chin. Chem. Lett. 2016; 27: 1505 Supplementary Material Supplementary Material Supporting Information
