The first method for protection-deprotection of the indole 2,3-pi bond.

نویسندگان

  • Phil S Baran
  • Carlos A Guerrero
  • E J Corey
چکیده

[reaction: see text] The scope and generality of a new reaction of indoles with MTAD is discussed. In most cases the ene-type reaction proceeds within seconds or minutes at 0 degrees C to provide the urazole adducts in high yield. This reaction provides the first method for protecting the indole 2,3-double bond since the urazole adducts can be reconverted to the starting indole (retro-ene) simply by heating.

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

A Facile and Environmental Friendly Method for C=N Bond Cleavage of Imines Using p-Toluenesulfonic Acid in Solid State

A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. ...

متن کامل

Ammonium Decatungstocerate(IV): An Efficient Catalyst for the Protection and Deprotection of Tetrahydropyranyl Ethers

In multi-step organic syntheses, the protection and deprotection of tetrahydropyranyl (THP) ethers is one of the most frequently used methods. Over the years, different methods have been used from various catalytic systems for the protection of hydroxyl groups as THP ethers and their deprotection. Herein we have reported that various alcohols and phenols have been efficiently converted to the c...

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

Palladium on carbon-catalyzed synthesis of 2- and 2,3-substituted indoles under heterogeneous conditions.

A mild, efficient and LiCl-free synthetic method for indole derivatives based on the heteroannulation of alkynes with 2-iodoanilines was achieved using palladium on carbon (Pd/C) and NaOAc in heated NMP. The N-tosyl protection of 2-iodoaniline expedited the reaction progress, while other protecting groups, such as tert-butoxycarbonyl, acetyl, and benzyloxycarbonyl groups, underwent deprotection...

متن کامل

Cerium(IV) as Ceric Triethylammonium Nitrate: An Efficient Catalyst for Protection and Deprotection of Alcohols with Dihydropyran

Catalytic amount of Ce(IV) as ceric triethylammonium nitrate (CTEAN) in dichloromethane or acetone can bring about an efficient tetrahydropyranylation of different types of alcohols to afford the corrsesponding tetrahydropyranyl ethers in high yields. Deportection of tetrahydropyranyl ethers can also be achieved efficiently in the presence of this catalyst in methanol.

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 letters

دوره 5 11  شماره 

صفحات  -

تاریخ انتشار 2003