Pd(II)-catalyzed ligand controlled synthesis of methyl 1-benzyl-1H-indole-3-carboxylates and bis(1-benzyl-1H-indol-3-yl)methanones.

نویسندگان

  • Rong Shen
  • Taichi Kusakabe
  • Keisuke Takahashi
  • Keisuke Kato
چکیده

A simple change of ligand and solvent allows controlled, effective switching between cyclization-carbonylation and cyclization-carbonylation-cyclization-coupling (CCC-coupling) reactions of 2-alkynylanilines catalyzed by palladium(II). The use of a [Pd(tfa)2(box)] catalyst in iPrOH afforded symmetrical ketones bearing two indoles in good yields; replacing the catalyst and solvent with Pd(tfa)2 and DMSO-MeOH led to the formation of methyl 1-benzyl-1H-indole-3-carboxylates in good yields.

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

Catalyst and Solvent-Free Microwave Assisted Expeditious Synthesis of 3-Indolyl-3-hydroxy Oxindoles and Unsymmetrical 3,3-Di(indolyl)indolin-2-ones

A simple and efficient method for the synthesis of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2-ones using microwave irradiation without catalyst and solvent is described. A series of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2ones have been synthesized in very short reaction times of 5 and 10 minutes and in yields ranging from 31% to 98%...

متن کامل

Bis{benzyl 3-[(1H-indol-3-yl)methyl­idene]dithio­carbazato-κ2 N 3,S}palladium(II) pyridine disolvate

The Pd(II) ion in the title compound, [Pd(C(17)H(14)N(3)S(2))(2)]·2C(5)H(5)N, is located on an inversion center and is four-coordinated by two of the deprotonated N,S-bidentate Schiff base ligands in a square-planar geometry. The dihedral angle between the aromatic ring planes within the ligand is 71.12 (9)°. The indole NH groups are bonded to the pyridine solvent mol-ecules via an N-H⋯N inter-...

متن کامل

Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction.

The CuI- or Ag₂CO₃-catalyzed [3+2] cycloaddition of propargyl-substituted dihydroisoindolin-1-one (3) with arylnitrile oxides 1a-d (Ar = Ph, p-MeC₆H₄, p-MeOC₆H₄, p-ClC₆H₄) produces in good yields novel 3,5-disubstituted isoxazoles 4 of the ethyl-2-benzyl-3-oxo-1-((3-arylisoxazol-5yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylate type. With aryl azides 2a-d (Ar = Ph, p-MeC₆H₄, p-OMeC₆H₄, p-ClC₆H...

متن کامل

(Z)-Methyl 4-[3-(3-oxoquinuclidin-2-yl­idenemeth­yl)-1H-indol-1-ylmeth­yl]benzoate

The title compound, C(25)H(24)N(2)O(3) was prepared by the reaction of (Z)-2-(1H-indol-3-ylmethyl-ene)-1-aza-bicyclo-[2.2.2]octan-3-one with methyl p-(bromo-meth-yl)benzoate, under phase-transfer catalytic (PTC) conditions using triethyl-benzyl-ammonium chloride and 50% w/v aqueous NaOH solution in dichloro-methane. The crystal structure indicates the presence of a double bond with Z geometry c...

متن کامل

Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives.

Starting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b), pyrano(2,3-d)imida-zole (8a, b and 9a, b), 2-substituted quinoxaline (11a, b-17a, b) and triazolo(4,3-a)quinoxaline derivatives (18a, b and 19a, b) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial a...

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 12 26  شماره 

صفحات  -

تاریخ انتشار 2014