Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles.

نویسندگان

  • Thomas B Parsons
  • Cédric Ghellamallah
  • Louise Male
  • Neil Spencer
  • Richard S Grainger
چکیده

Treatment of methyl indole-3-carboxylate with bromine in acetic acid gives methyl 5,6-dibromoindole-3-carboxylate regioselectively, from which the parent 5,6-dibromoindole can be accessed via a one-pot, microwave-mediated ester hydrolysis and decarboxylation. Application of these building blocks in syntheses of natural and non-natural 5,6-dibromoindole derivatives, including meridianin F and 5,6-dibromo-2'-demethylaplysinopsin, is reported.

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

Application of Poly(N, N′- dibromo-N-ethyl-naphthyl-2,7-disulfonamide) for the Regioselective Synthesis of New 3-Sulfenyl Indole Derivatives

Electron-rich aza-aromatic compounds such as indoles is structures of particular interest and importancein organic chemistry. A useful procedure for the preparation of new 3-sulfenyl indole derivatives using S-alkyl or S-arylthiophthalimides as sulfenylating agents and poly(N, N′-dibromo-N-ethyl-naphthyl-2,7-disulfonamide) as novel catalyst is described. The method represents an efficient prepa...

متن کامل

A NEW STRATEGY FOR THE SYNTHESIS OF TRICYCLIC AND TETRACYCLIC SYSTEMS OF INDOLE ALKALOIDS

Reaction of tryptamine 1 with dimethyl -3-methoxyallylidenemalonate 2 afforded N?-[4,4-bis (methoxycarbonyl)-1,3-butadienyl] tryptamine 3 which in combination with acetylchloride and pyridine in dichloromethane gave N?, N?-[acetyl]-[(4,4-dinethoxycarbonyl) 1,3butadienyl] tryptamine 4. Treatment of 3 with sodium hydroxide afforded 2H[N-(3-indolyl) ethyl] 2-oxo-3-methoxycarbonyl-1-pyridine 5. Cy...

متن کامل

Application of Nicotinic Acid Functionalized Chlorosulfonic Acid as a Green Catalyst for the Synthesis of Bis(2-methyl-1Hindole)Derivatives

3-Carboxy-1-sulfopyridin-1-ium chloride ([CPySO3H]+Cl-) as a novel ionic organocatalyst for thecondensation of aldehydes and 2-methylindole to synthesize bis(2-methyl-1H-indole) derivatives inacetonitrile at room temperature has been developed. Some tetrakis (2-methyl-1H-indole)derivatives have also been synthesized by the reaction of 2,2'-(butane-1,4-diylbis(oxy))dibenzaldehyde and 2-methylind...

متن کامل

Fe3O4 magnetic nanoparticles (MNPs) as an effective catalyst for synthesis of indole derivatives

The principal aim of this research is the application of Fe3O4 (MNPs) in the synthesis of some indole derivatives. Fe3O4 MNPs were prepared by Co-Precipitation method from the reaction of FeCl2.4H2O and FeCl3.6H2O in ammonia solution. Morphology and structure of Fe3O4 MNPs were determined by FT-IR, X-Ray diffraction (XRD), transmission electron microscopy (TEM) and scanning electron microscopy ...

متن کامل

Triphenylphosphine mediated synthesis of functionalized aryl-vinyl ethers from7-hydroxy coumarin and methyl acetylene carboxylate

7-hydroxy coumarin undergoes neutral conditions with alkyl propiolates in the presence of triphenylphosphine, and bysubstituation the corresponding aryl vinyl ethers was obtained in good yields

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 9 14  شماره 

صفحات  -

تاریخ انتشار 2011