N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes.

نویسندگان

  • Mahesh H Shinde
  • Umesh A Kshirsagar
چکیده

An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.

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

An efficient one-pot synthesis of α-amino nitriles using ecofriendly Lewis-acidic ionic liquid choline chloride.2ZnCl2

α-Amino nitriles are synthesized in a one-pot, three-component coupling of aldehydes (or ketones), aniline, and trimethylsilyl cyanide using a catalytic amount of choline chloride.2ZnCl2 as a bio Lewis acidic ionic liquid. Mild Lewis acidic characteristic of this ionic liquid allows efficient synthesis of α-amino nitriles from acid sensitive aldehydes.

متن کامل

An efficient one-pot synthesis of α-amino nitriles using ecofriendly Lewis-acidic ionic liquid choline chloride.2ZnCl2

α-Amino nitriles are synthesized in a one-pot, three-component coupling of aldehydes (or ketones), aniline, and trimethylsilyl cyanide using a catalytic amount of choline chloride.2ZnCl2 as a bio Lewis acidic ionic liquid. Mild Lewis acidic characteristic of this ionic liquid allows efficient synthesis of α-amino nitriles from acid sensitive aldehydes.

متن کامل

Brønsted acidic ionic liquid as a metal free catalyst for the one-pot synthesis of α-aminonitriles under mild and solvent-free conditions

An efficient, mild and environmentally friendly method was developed for the Strecker reaction to synthesize α-aminonitriles in the presence of methyl imidazolium hydrogen sulfate ([Hmim][HSO4]) as an efficient catalyst. These syntheses were performed via a one-pot three-component condensation of aldehydes (or ketones), amines, and trimethylsilyl cyanide under mild and solvent free c...

متن کامل

Brønsted acidic ionic liquid as a metal free catalyst for the one-pot synthesis of α-aminonitriles under mild and solvent-free conditions

An efficient, mild and environmentally friendly method was developed for the Strecker reaction to synthesize α-aminonitriles in the presence of methyl imidazolium hydrogen sulfate ([Hmim][HSO4]) as an efficient catalyst. These syntheses were performed via a one-pot three-component condensation of aldehydes (or ketones), amines, and trimethylsilyl cyanide under mild and solvent free c...

متن کامل

One-Pot Synthesis of Some New α-Bromoketals and Acetals via 1,8-Diazabicyclo[5.4.0] Undec-7-ene-Hydrobromide-Perbromide

α-Bromoketals and acetals are important synthetic precursors in organic synthesis. In this work, some new α-bromoketals are synthesized by the reaction of aryl methyl ketones with diols in the presence of 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) hydrobromide-perbromide in good isolated yields. The latter compound converts aldehydes to acetals and serves as a new and efficient reagent for t...

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 3  شماره 

صفحات  -

تاریخ انتشار 2016