891186-75-7Relevant academic research and scientific papers
A 2-indolone-3-carboxylic acid ester derivative synthesis method
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, (2017/02/24)
The invention discloses a synthesis method of 2-indolone-3-carboxylate derivatives (I), which comprises the following steps: reacting substituted aniline (II) used as a raw material and triethylamine as an acid-binding agent with ethyl malonyl chloride (III) to generate ethyl malonyl chloride (IV); reacting the ethyl malonyl chloride (IV) with acetyl chloride in an acetonitrile-tetrahydrofuran mixed solution under the action of sodium hydride to generate an enol form compound (V); carrying out intramolecular cyclization on the enol form compound (V) under the action of iodosobenzene diacetate to remove acetyl group, thereby obtaining 2-indolone-3-carboxylate; and reacting the 2-indolone-3-carboxylate with triisopropyl trifluoromethanesulfonates under the action of triethylamine to generate the 2-indolone-3-carboxylate derivatives (I). The synthesis method is simple to operate, and has the advantages of mild reaction conditions, accessible reaction raw materials and reaction reagents, no need of toxic metal reagents, environment friendliness and the like.
Metal-free synthesis of 2-oxindoles via PhI(OAc)2-mediated oxidative C-C bond formation
Lv, Jinglei,Zhang-Negrerie, Daisy,Deng, Jun,Du, Yunfei,Zhao, Kang
, p. 1111 - 1119 (2014/03/21)
The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions between anilide 1 and phenyliodine(III) diacetate (PIDA) through hypervalent iodine mediated C(sp2)-C(sp2) bond formation followed by a subsequent deacylation reaction. This metal-free method, shown to provide direct access to an important oxindole intermediate, could be applied to the total synthesis of naturally occurring horsfiline.
Regioselective access to substituted oxindoles via rhodium-catalyzed carbene C-H insertion
Gauthier, Delphine,Dodd, Robert H.,Dauban, Philippe
experimental part, p. 8542 - 8555 (2009/12/24)
Rhodium-catalyzed decomposition of diazoamides followed by insertion of the resulting carbenes into an aromatic C-H bond gives access to substituted oxindoles. The reaction takes place with aromatic rings substituted by either electron-donating or -withdrawing groups at ortho, meta or para positions and the regioselectivity can be controlled by a substitution α to the diazo functionality. In the presence of an ester, the reaction leads to the formation of 2-silyloxyindole-3-carboxylates in 40-85% yields and regioselectivities up to 80% are observed in the case of meta-substituted substrates. This selectivity mainly relies on steric factors and use of a more bulky N,N-diethylamide then affords 2-silyloxyindole-3-carboxamides in 42-91% yields with complete regioselectivity.
Palladium asymmetric allylic alkylation of prochiral nucleophiles: Horsfiline
Trost, Barry M.,Brennan, Megan K.
, p. 2027 - 2030 (2007/10/03)
The asymmetric synthesis of the oxindole alkaloid horsfiline is described. A palladium-catalyzed asymmetric allylic alkylation (AAA) is used to set the spiro(pyrrolidine-oxindole) stereogenic center.
