Synthesis of (E)-oxindolylidene acetate using tandem palladium-catalyzed Heck and alkoxycarbonylation reactions.

نویسندگان

  • Wei-Jen Lin
  • Kak-Shan Shia
  • Jen-Shin Song
  • Ming-Hsien Wu
  • Wen-Tai Li
چکیده

Tandem reactions use consecutive reaction steps to efficiently synthesize compounds of high molecular complexity. This paper presents a tandem Pd-catalyzed Heck and alkoxycarbonylation reaction for the stereoselective synthesis of (E)-oxindolylidene acetates. The mechanism underlying the Pd-catalyzed tandem reaction involves the syn-carbopalladation of ynamides followed by alkoxycarbonylation with CO and alcohol. This method makes it possible to obtain the desired (E)-configuration of oxindolylidene acetates exclusively. We evaluated the scope of the reaction by applying optimal reaction conditions to the facile synthesis of a library of (E)-oxindolylidene acetates. The resulting (E)-oxindolylidene acetates exhibited potent anticancer activities against a variety of human cancer cell lines. The anticancer activities of some (E)-oxindolylidene acetates were even superior to those of known CDK inhibitors indirubin-3'-oxime and roscovitine.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Heck, direct arylation, and hydrogenation: two or three sequential reactions from a single catalyst.

Palladium-catalyzed tandem multifunctional reactions leading to the synthesis of substituted biaryl molecules have been developed including tandem Heck-direct arylation and tandem-sequential Heck-direct arylation-hydrogenation. These reactions occur in good yield and have been employed in the synthesis of a cytotoxic biaryl compound.

متن کامل

Synthesis, Characterization and Catalytic Activity of Ligand Stabilized Palladium Nanoparticle: A Catalyst Compliment to the Heck Coupling Reaction

The palladium metal is the most frequently used metal because of its excellent catalytic efficiency and most flexible varying oxidation state. So,  we report  that palladium nanoparticles (Pd NPs) stabilized by a ligand (o-vanilindiphenylethanedionedihydrazone, L)  using reverse micelles method have been synthesized, while all particles are in spherical shape and ranging between 10 and...

متن کامل

Polystyrene Supported [N-(Alanine) Sulfonamide]/Palladium Chloride: Synthesis, Characterization, for Heck Coupling Reactions

Abstract As a monomer, the [N-(alanine)] para-styrene sulfonamide (ASS) was prepared, from the reaction of para-styrene sulfonyl chloride and (S)-(+)-alanine in the presence of KOH 1M as a base, and CH3Cl was used as solvent. The monomer confirmed using FT-IR and 1H-NMR spectroscopy. Polystyrene [N-(alanine) sulfonamide] (PASS) was also prepared from the polymerization of [N-(alanine)] pa...

متن کامل

The synthesis of some perhydrobenzimidazolinium salts and their application in pd-carbene catalyzed heck and suzuki reactions.

Novel 1,3-dialkylperhydrobenzimidazolinium chloride salts were prepared as precursors of N-heterocyclic carbenes 3a-e by reacting N,N'-dialkylcyclohexandiamine, triethyl orthoformate and ammonium chloride. The salts were characterized spectroscopically and the complexes formed in situ from Pd(OAc)2 and 3 have been tested as catalysts in homogenous Heck and Suzuki reactions.

متن کامل

Synthesis of functionalized aryl-alkenes catalyzed by CN-ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime under microwave irradiation

A new dimeric orthopalladated complex was synthesized via reaction of 2,3-dimethoxy benzaldehyde oxime with palladium chloride and lithium chloride in methanol as solvent and sodium acetate as base at room temperature. The catalytic activity of this dimeric [Pd{C6H2(-CH=NOH)-(OMe)2-2,3}(µ-Cl)]2 complex as an efficient, air, and moisture tolerant catalyst was investigated in Mizoroki–Heck cross ...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 14 1  شماره 

صفحات  -

تاریخ انتشار 2016