Synlett, Inhaltsverzeichnis Synlett 2020; 31(01): 77-82DOI: 10.1055/s-0039-1691488 letter © Georg Thieme Verlag Stuttgart · New YorkRhodium(III)-Catalyzed Regioselective C7-Allylation of Indazoles Autoren Jiyou Huo Hongshun Yuan Lanting Xu ∗ Xianhua Pan∗ Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract An efficient rhodium-catalyzed regioselective C–H allylation of N,N-diisopropylcarbamoyl indazoles with allylic carbonates as allylating agents has been developed. This methodology provides facile access to C7-allylated indazoles with high regioselectivity, ample substrate scope and broad functional group tolerance. Key words Key wordsindazoles - C–H activation - regioselectivity - allylation - rhodium catalysis Volltext Referenzen References and Notes 1 New address: College of Chemistry and Materials Science, Shanghai Normal University, No. 100 Guilin Rd., Shanghai 200234, P. R. of China. 2a Ali NA. 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After cooling to room temperature, the reaction mixture was purified by chromatography on silica with a gradient eluent of petroleum ether and ethyl acetate to give the corresponding product. 7-Allyl-N,N-diisopropyl-1H-indazole-1-carboxamide (3aa): Yield: 82% (46.7 mg); white solid. 1H NMR (500 MHz, CDCl3): δ = 8.07 (s, 1 H), 7.61 (d, J = 7.9 Hz, 1 H), 7.27 (d, J = 7.1 Hz, 1 H), 7.19 (t, J = 7.5 Hz, 1 H), 6.06–6.00 (m, 1 H), 5.07 (d, J = 10.1 Hz, 1 H), 4.96 (d, J = 17.2 Hz, 1 H), 4.12 (brs, 1 H), 3.77 (d, J = 4.7 Hz, 2 H), 3.61 (brs, 1 H), 1.56 (brs, 6 H), 1.26 (brs, 6 H). 13C NMR (125 MHz, CDCl3): δ = 151.62, 139.15, 136.55, 136.18, 128.91, 125.84, 124.68, 122.73, 119.02, 116.28, 51.36, 46.29, 36.71, 20.59, 20.08. HRMS (ESI): m/z [M + H]+ calcd for C17H24N3O+: 286.19139; found: 286.19119. Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window) Primärdaten Primary Data (ZIP) (opens in new window)
