By Yusuke Ohta
A copper-catalyzed direct synthesis of 2-(aminomethyl)indoles by means of catalytic domino response together with multi-component coupling used to be built, and is the 1st instance of a three-component indole formation with no generating salts as a byproduct. in line with this response, a copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline was once comprehensive which represents an unheard of isoquinoline synthesis via a four-component coupling response. Following those effects, large program reviews utilizing one-pot palladium-, acid-, or base-promoted cyclization published that indole- or isoquinoline-fused polycyclic compounds might be effortlessly synthesized via multi-component reactions. because the proposal of eco-friendly Chemistry turns into ever extra vital, those findings could provide effective and atom-economical methods to the diversity-oriented synthesis of bioactive compounds containing a fancy constitution. this would result in improvement of promising drug leads with structural complexity. The paintings of this thesis will cross directly to encourage the bogus learn of many readers.
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Additional resources for Copper-Catalyzed Multi-Component Reactions: Synthesis of Nitrogen-Containing Polycyclic Compounds
Sample text
The compounds S7a–e, S9, and S10a, b are commercially available. The compounds S7a [39], S7b [40], S7c [41], S7d [42], S9d [43], and S12 [44] are known. 5 h at this temperature. The reaction mixture was stirred at 80 °C for 15 h. After concentration under reduced pressure, the residue was extracted with Et2O. The extract was washed successively with aqueous saturated NaHCO3 and brine, and dried over MgSO4. 7. Anal. 96. 72. 30 mmol) at rt under argon, and the reaction mixture was stirred for at 80 °C 12 h.
The compounds S7a [39], S7b [40], S7c [41], S7d [42], S9d [43], and S12 [44] are known. 5 h at this temperature. The reaction mixture was stirred at 80 °C for 15 h. After concentration under reduced pressure, the residue was extracted with Et2O. The extract was washed successively with aqueous saturated NaHCO3 and brine, and dried over MgSO4. 7. Anal. 96. 72. 30 mmol) at rt under argon, and the reaction mixture was stirred for at 80 °C 12 h. The mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography over silica gel with hexane–EtOAc (10:1) to give S3 (206 mg, 43%) as a colorless solid.
The reaction proceeded cleanly to afford tetrahydropyridine-fused indole 9a in 47% yield. When DMA was used as the reaction solvent, a higher yield of 9a was observed (65%, entry 2). Further investigation of the palladium catalyst, ligand, and base (entries 3–5) revealed that the conditions shown in entry 2 were most effective. 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).
