20973-67-5Relevant articles and documents
CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence
Ye, Yuxuan,Kim, Seoung-Tae,Jeong, Jinhoon,Baik, Mu-Hyun,Buchwald, Stephen L.
, p. 3901 - 3909 (2019)
Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)indoles, as coupling partners. N- or C3-alkylated indoles are prepared with high levels of regio- and enantioselectivity using a copper hydride catalyst. The regioselectivity is governed by the use of either DTBM-SEGPHOS or Ph-BPE as the supporting ligand. Density functional theory (DFT) calculations are conducted to elucidate the origin of the ligand-controlled regiodivergence.
TFA-catalysed tandem double cyclisation: A one-pot, metal-free routes for novel indolo-imidazo[1,2-a]pyridine derivatives
Ganesher, Asha,Panda, Gautam
supporting information, (2019/11/11)
A transition-metal free, one-pot tandem synthetic routes for novel indole and imidazo[1,2-a]pyridine derivative hybrids have been established. An efficient three-component reaction was designed with incorporation of two sequential Groebke–Blackburn–Bienay
Enamine compound synthesis method and aromatic aldehydes synthetic method of the compound (by machine translation)
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Paragraph 0064; 0065; 0066; 0067; 0068, (2017/12/09)
The invention provides a method for synthesis of a enamine compound and aromatic aldehydes synthetic method of the compound. Enamine compound of synthetic method comprises the starting raw materials with A N, N - dimethyl formamide dimethyl acetal to form a mixed solution; and the mixed solution is continuously fed into the continuous reactor in the alkene amination reaction to obtain the enamine compound B, and alkene amination reaction in continuous enamine compound discharged from the continuous reactor in B; A starting material of formula (1) shown in the structural formula of, enamine compound B formula (2) shown in the structural formula. The reaction of the raw material of the mixed solution and continuously fed into the reactor by way of the alkene amination reaction alkene amination reaction of continuous, then also the continuous production of aromatic aldehyde compound, shortens the reaction time, the reaction efficiency is improved. The continuous reaction method can be stopped at any time according to the actual conditions the reaction or the termination of the reaction, after-treatment can also be based on the need to batch processing or merging processing, is convenient and simple. (by machine translation)
