81803-90-9Relevant academic research and scientific papers
Cu-catalyzed cyclization to construct indoles fromN-(ortho-chloromethyl)aryl carbamates and terminal alkynesviaa one-pot reaction
Shi, Yang,Wang, Gangqiang,Wang, Hang,Deng, Bin,Gao, Tao,Wang, Jian,Guo, Haibing,Wu, Minghu,Sun, Shaofa
supporting information, p. 14477 - 14480 (2020/09/21)
In this reaction, a new strategy for the synthesis of indoles fromN-(ortho-chloromethyl)aryl carbamates and terminal alkynesviaCu-catalyzed coupling-cyclization has been developed. The reactions proceeded smoothly under mild conditions with a wide functional group tolerance.
Polysubstituted indole derivative and metal catalytic preparation method thereof
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Paragraph 0060-0062, (2020/08/18)
The invention provides a polysubstituted indole derivative and a metal catalytic preparation method thereof, and belongs to the technical field of medicines. The structural formula of the polysubstituted indole derivative is shown in the specification. The method comprises the following steps: adding a catalytic amount of a metal catalyst into a container filled with a substituted o-aminobenzyl halide compound and a substituted alkyne compound, adding a proper solvent, stirring and reacting at the reaction temperature of 25-100 DEG C for 4 hours, adding equivalent alkali into the reaction solution, filtering after the reaction is finished, washing filtrate with water or a saturated edible salt solution, extracting with an organic solvent, drying, carrying out reduced pressure distillationand concentration to remove the solvent, and carrying out column chromatography separation on the crude product. The method has the advantages of high product selectivity and yield and the like.
Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via Sigmatropic Rearrangement
Mohri, Kunihiko,Oikawa, Yuji,Hirao, Ken-ichi,Yonemitsu, Osamu
, p. 3097 - 3105 (2007/10/02)
Phenylhydroxylamine (13) oxalate was quite easily acylacetylated by heating with an equimolar amount of acyl Meldrum's acid (4) in acetonitrile to give an N-acylacetylphenylhydroxylamine (14) in high yield.When 14 was treated with another equimolar amount of the same 4 in refluxing toluene, a series of reactions, O-acylacetylation, 1-aza-1'-oxasigmatropic rearrangement, decarboxylation, dehydrative cyclization, and deacylation, occured consecutively to give a 2-substituted indole (16) in fair yield, though sometimes accompanied by the formation of a 5-substituted 4-isoxazolin-3-one (17).N-Benzoyl, N-acetyl, and N-benzyloxycarbonyl derivatives of phenylhydroxylamine (18) were treated with phenylacetyl Meldrum's acid (4i) in refluxing benzene containing copper powder to give readily rearranged ortho alkylation products (19), which were converted to the corresponding N-acyl-2-benzylindoles (20) by treatment with hydrochloric acid in boiling ethanol or with anhydrous p-toluenesulfonic acid in benzene at room temperature.Keywords - acyl Meldrum's acid; phenylhydroxylamine; N-acylacetylphenylhydroxylamine; 2-substituted indole; 1-aza-1'-oxasigmatropic rearrangement; acid-catalyzed cyclization
MELDRUM'S ACID IN ORGANIC SYNTHESIS 3. SYNTHESIS OF 2-SUBSTITUTED INDOLES FROM PHENYLHYDROXYLAMINE
Mohri, Kunihiko,Oikawa, Yuji,Hirao, Ken-ichi,Yonemitsu, Osamu
, p. 515 - 520 (2007/10/02)
Treatment of phenylhydroxylamine oxalate with acyl Meldrum's acids in boiling acetonitrile readily gave N-acylacetylphenylhydroxylamines, which were converted to 2-substituted indoles by another treatment with acyl Meldrum's acids in refluxing toluene.N-B
