1616706-98-9Relevant academic research and scientific papers
Borane-catalyzed indole synthesis through intramolecular hydroamination
Tussing, Sebastian,Ohland, Miriam,Wicker, Garrit,Fl?rke, Ulrich,Paradies, Jan
, p. 1539 - 1545 (2017)
The reaction of 2-alkynyl anilines with catalytic amounts of B(C6F5)3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of tetrahydroquinoline 8 in good yield.
Indazole 2-oxides compound and method for preparing indazole 2-oxides compound for providing a nitrogen heterocyclic compound used as a precursor for drugs
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Paragraph 0020; 0040-0042, (2019/08/28)
Provided is a method for preparing an indazole 2-oxides compound, which comprises the step of: performing a cyclization reaction on 2-alkynyl aniline compound and tert-butylnitrite represented by formula (1) in the presence of bis(dibenzylideneacetone) palladium so as to produce an indazole 2-oxides compound, in which, in the formulae (1) and (2), R1 , R2 , R3 and R4 are each hydrogen, halogen or alkyl group; X1 represents an alkyl group, a first chemical structure, a second chemical structure or a third chemical structure where T1 , T2 , T3 , T4 and T5 are each hydrogen, halogen, alkoxy group, or alkyl group; X2 represents hydrogen, cycloalkyl group, alkyl group, alkenyl group, thienyl group, unsubstituted phenyl group, or substituted phenyl group, where the substituent is selected from the group consisting of an alkyl group, an alkoxy group, a halogen, a haloalkyl group, -CN, or -NO2.
Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides
Senadi, Gopal Chandru,Wang, Ji-Qi,Gore, Babasaheb Sopan,Wang, Jeh-Jeng
, p. 2747 - 2753 (2017/08/23)
An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo
Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides
Le, Christine M.,Sperger, Theresa,Fu, Rui,Hou, Xiao,Lim, Yong Hwan,Schoenebeck, Franziska,Lautens, Mark
, p. 14441 - 14448 (2016/11/13)
We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. Calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.
