Copper-Catalyzed Multi-Component Reactions: Synthesis of by Yusuke Ohta

By Yusuke Ohta

A copper-catalyzed direct synthesis of 2-(aminomethyl)indoles by way of catalytic domino response together with multi-component coupling used to be constructed, and is the 1st instance of a three-component indole formation with no generating salts as a byproduct. according to this response, a copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline was once complete which represents an remarkable isoquinoline synthesis via a four-component coupling response. Following those effects, vast software reports utilizing one-pot palladium-, acid-, or base-promoted cyclization published that indole- or isoquinoline-fused polycyclic compounds may be conveniently synthesized via multi-component reactions. because the inspiration of eco-friendly Chemistry turns into ever extra vital, those findings may supply effective and atom-economical ways to the diversity-oriented synthesis of bioactive compounds containing a fancy constitution. this may result in improvement of promising drug leads with structural complexity. The paintings of this thesis will cross directly to encourage the substitute learn of many readers.

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20 mmol) at 0 °C for 5 min. The reaction mixture was quenched with aqueous saturated citric acid, and the whole was extracted with EtOAc. The extract was washed successively with H2O, aqueous saturated NaHCO3, and brine, and dried over MgSO4. 7. Anal. 13. 14. 80 g, 77%). 6. Anal. 25. 31. 77 g, quant). 0. Anal. 91. 91. 70 g, 76%) by the reaction under reflux for 16 h. 7. Anal. 13. 12. 40 g, 90%) as colorless crystals. 8. Anal. 66. 66. 8. Anal. 25. 30. 20 mmol) at rt under argon, and the reaction mixture was stirred at 80 °C for 15 min.

Encouraged by this result, the author investigated the reaction with several 2(aminomethyl)indoles containing an electron-withdrawing and -donating group to obtain variously substituted tetrahydropyridine-fused indoles 9b–f in moderate to good yields (Table 7). The author next examined construction of polycyclic indoles by palladiumcatalyzed C–H arylation using 2-(aminomethyl)indole 7x, which was prepared from ethynylaniline 1a and amine 3h (Table 5, entry 11). % of PPh3, dihydrobenzazepine-fused indole 10 was efficiently obtained in 80% yield over 2 steps (Scheme 3).

5 mL) at 0 °C. 5 h at this temperature. After concentration under reduced pressure, the residue was quenched with aqueous saturated NaHCO3. The whole was extracted with CH2Cl2, and the extract was dried over MgSO4. 0. Anal. 60. 50. 0034 mmol) at rt under argon. The reaction mixture was stirred at 80 °C for 50 min. 1632. TsCl pyridine 2. 5 h at this temperature. The mixture was filtered through a pad of Celite. 30 g, 96%). 73 mmol) at 0 °C under argon and the reaction mixture was stirred overnight at rt.

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