Synlett, Table of Contents Synlett 2019; 30(07): 851-856DOI: 10.1055/s-0037-1611754 letter © Georg Thieme Verlag Stuttgart · New YorkDirect N-sec-Alkylation of Amides by Reaction of α-Halohydroxamates and Sulfonylindoles: An Approach to 3-Indolyl Methanamines Authors Author Affiliations Yuan Chen a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China b College of Chemistry and Chemical Engineering, China West Normal University, Nanchong City 637002, P. R. of China Email: kangtairan@sina.com Xiaoqiang Guo a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China Chuang Zhou a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China Lianmei Chen a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China Tairan Kang * a College of Pharmacy and Biological Engineering, Chengdu University, Chengdu City 610106, P. R. of China b College of Chemistry and Chemical Engineering, China West Normal University, Nanchong City 637002, P. R. of China Email: kangtairan@sina.com Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A catalyst-free, base-mediated N-sec-alkylation of amides by reaction of sulfonylindoles and α-halohydroxamates has been developed. The N-sec-alkylation of amides reaction is based on an intermolecular nucleophilic addition of vinylogous imine with N-(benzyloxy)meth-acrylamide/azaoxyallyl cations formed in situ and represents a simple way to give polyfunctionalized 3-indolyl methanamines in good to excellent yields. Key words Key words3-indolyl methanamines - azaoxyallyl cations - vinylogous imine - sulfonylindoles - α-halohydroxamates Full Text References References and Notes 1a Somei M, Yamada F. Nat. Prod. Rep. 2004; 21: 278 1b Faulkner DJ. Nat. Prod. Rep. 2002; 19: 1 1c Shirakawa S, Kobayashi S. Org. Lett. 2006; 8: 4939 1d Sidhu PS, Nassif N, McCallum MM, Teske K, Feleke B, Yuan NY, Nandhikonda P, Cook JM, Singh RK, Bikle DD, Arnold LA. ACS Med. Chem. Lett. 2014; 5: 199 1e Sidhu PS, Teske K, Feleke B, Yuan NY, Guthrie ML, Fernstrum GB, Vyas ND, Han L, Preston J, Bogart JW, Silvaggi NR, Cook JM, Singh RK, Bikle DD, Arnold LA. Cancer Chemother. Pharm. 2014; 74: 787 1f Bao B, Sun Q, Yao X, Hong J, Lee C.-O, Sim CJ, Im KS, Jung JH. J. Nat. Prod. 2005; 68: 711 1g Bao B, Sun Q, Yao X, Hong J, Lee C.-O, Cho HY, Jung JH. J. Nat. Prod. 2007; 70: 2 1h Feussner K.-D, Ragini K, Kumar R, Soapi KM, Aalbersberg WG, Harper MK, Carte B, Ireland CM. Nat. Prod. 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The crude product was purified by flash column chromatography on silica gel [flash column chromatography eluent, petroleum ether/ethyl acetate (6:1–4:1, v/v)] to give the pure product 3a (37 mg, 91% yield) as an oil. 1H NMR (400 MHz, CDCl3): δ = 7.37–7.34 (m, 3 H), 7.30–7.27 (m, 3 H), 7.23–7.21 (m, 1 H), 7.16–7.13 (m, 3 H), 7.11–7.08 (m, 1 H), 6.96–6.92 (m, 1 H), 6.77 (d, J = 6.94 Hz, 2 H), 5.48 (s, 1 H), 5.35 (s, 1 H), 4.95 (s, 1 H), 4.59 (d, J = 8.68 Hz, 1 H), 3.96 (d, J = 8.70 Hz, 1 H), 2.20 (s, 3 H), 2.06 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 171. 4, 141.1, 139.9, 135.1, 134.9, 134.4, 129.5, 129.3, 128.6, 128.5, 128.4, 128.3, 128.1, 127.0, 126.8, 121.3, 119.8, 119.7, 117.3, 110.3, 108.7, 78.6, 57.4, 20.4, 12.5. HRMS: m/z [M+H]+ calcd for C27H26N2O2: 410.2013; found: 410.2016. 15 CCDC 1546337 (3g) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif. Supplementary Material Supplementary Material Supporting Information (PDF) CIF File (ZIP)
