Synlett, Inhaltsverzeichnis Synlett 2024; 35(20): 2385-2390DOI: 10.1055/a-2316-5200 letter Special Issue to Celebrate the 75th Birthday of Prof. B. C. Ranu One-Pot Expeditious Synthesis of Pyrazoloindolones via Base-Promoted Electrocyclization, C–N Coupling and Intramolecular Oxidative Cyclization Autor*innen Harshita Singh Korawat Manoj Kumar Saini Karmdeo Prajapati Maya Shankar Singh ∗ Ashok Kumar Basak∗ Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract Pyrazoloindolones are synthesized from N-tosylhydrazones in a one-pot multistep process which include base-promoted (i) electrocyclization reaction of N-tosylhydrazones derived from α,β-unsaturated aldehydes, (ii) aromatic nucleophilic substitution, and (iii) a domino cyclization–oxidation process under aerobic conditions. Key words Key words N-tosylhydrazone - electrocyclization - aromatic nucleophilic substitution - oxidative cyclization - pyrazoloindolones Volltext Referenzen References and Notes 1a Cherukupalli S, Karpoormath R, Chandrasekaran B, Hampannavar GA, Thapliyal N, Palakollu VN. Eur. J. Med. Chem. 2017; 126: 298 1b Kaswan P, Pericherla K, Purohit D, Kumar A. Tetrahedron Lett. 2015; 56: 549 1c Crossley EL, Issa F, Scarf AM, Kassiou M, Rendina LM. Chem. Commun. 2011; 47: 12179 1d Al-Adiwish WM, Tahir MI. M, Siti-Noor-Adnalizawati A, Hashim SF, Ibrahim N, Yaacob WA. Eur. J. Med. Chem. 2013; 64: 464 1e Selleri S, Bruni F, Costagli C, Costanzo A, Guerrini G, Ciciani G, Gratteri P, Besnard F, Costa B, Montali M, Martini C, Fohlin J, Siena GD, Aiello PM. J. Med. Chem. 2005; 48: 6756 1f Kamal A, Tamboli JR, Nayak VL, Adil SF, Vishnuvardhan MV. P. S. Bioorg. Med. Chem. Lett. 2013; 23: 3208 1g Ahmed OM, Mohamed MA, Ahmed RR, Ahmed SA. Eur. J. Med. 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The resulting mixture was placed in a pre-heated oil bath at 110 °C and stirred for 15 min. Then, 2-fluorobenzaldehyde 3a (24.8 mg, 0.20 mmol) and Cs2CO3 (146.6 mg, 0.45 mmol) were added, and the reaction mixture was stirred at 110 °C for 5 h. Then, the reaction mixture was purged with oxygen and heated at 130 °C under oxygen atmosphere (balloon) for 10 h. After cooling to rt, the reaction mixture was diluted with ethyl acetate (25 mL), extracted with brine (3 × 10 mL), dried over Na2SO4, and evaporated. The crude product was purified by silica gel column chromatography using 5% ethyl acetate in hexanes as eluent to obtain pyrazoloindolone 5a (32.1 mg, 65% yield) as a yellow-brown solid; mp 150–152 °C; Rf = 0.75 (0.5:9.5 ethyl acetate/hexane); purified using 2% ethyl acetate in hexanes as eluent. 1H NMR (500 MHz, CDCl3): δ = 7.76 (d, J = 6.5 Hz, 2 H), 7.53 (d, J = 6.5 Hz, 1 H), 7.45 (apt, J = 7.5 Hz, 1 H), 7.40–7.34 (m, 3 H), 7.29 (apt, J = 8.0 Hz, 1 H), 7.12 (apt, J = 8.0 Hz, 1 H), 6.86 (s, 1 H). 13C{1H} NMR (126 MHz, CDCl3): δ = 179.5, 157.9, 144.0, 139.7, 135.6, 132.0, 128.8, 128.7, 128.0, 126.3, 125.6, 124.9, 110.7, 103.3. HRMS (ESI-TOF): m/z calcd for C16H11N2O [M + H]+: 247.0871; found: 247.0842. Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window)
