Synthesis of amino-substituted indoles using the Bartoli reaction.

نویسندگان

  • Laura Wylie
  • Paolo Innocenti
  • Daniel K Whelligan
  • Swen Hoelder
چکیده

We report herein the concise preparation of a range of functionalised aminoindoles via a new application of the Bartoli reaction. Scope and limitations of the methodology have been extensively studied to reveal the importance of protecting groups and substitution patterns. The use of amino substituted nitroanilines for the Bartoli reaction is to our knowledge unprecedented. Our work thus represents a novel entry into substituted aminoindoles which are relevant building blocks for both the fine chemical and pharmaceutical industry.

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

[BMIm]HSO4 as a Green and Highly Efficient Catalyst for One-pot Synthesis of 3-Substituted Indoles under Ultrasound Irradiation

A practical and green synthesis of 3-substituted indoles is reported via three-component coupling reaction of indoles, aldehydes and N-methylaniline in the presence of the acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([BMIm]HSO4) under ultrasound irradiation at room temperature. The significant features of this procedure are high yields of the products, simple work-up, opera...

متن کامل

Total synthesis of indoles from Tricholoma species via Bartoli/heteroaryl radical methodologies.

The Bartoli indole synthesis is the treatment of an ortho-substituted nitro-aromatic compound with 3 equiv of vinylmagnesium bromide to give the 7-substituted indole,1,2 and this method has rapidly become the shortest and most flexible synthesis for indoles of this substitution pattern.1-5 We have recently reported an extension to this methodology, suggesting that it may not be limited exclusiv...

متن کامل

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 Clean and Highly Efficient Synthesis of Oxindole Substituted Pyrrolo[2,3-d]Pyrimidines under Ultrasound Irradiation

A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. All reactions performed effic...

متن کامل

One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A.

The reaction of (2-aminobenzyl) triphenylphosphonium bromide with aromatic aldehydes or alpha,beta-unsaturated aldehydes under microwave-assisted conditions constitutes a new synthesis of 2-substituted indoles in high yields (81-97%) in a one-pot reaction. The adduct from indole-4-carboxaldehyde was an advanced intermediate in the synthesis of arcyriacyanin 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 10 22  شماره 

صفحات  -

تاریخ انتشار 2012