An intramolecular cascade cyclization of 2-aryl indoles: efficient methods for the construction of 2,3-functionalized indolines and 3-indolinones.

نویسندگان

  • Arun K Ghosh
  • Zhi-Hua Chen
چکیده

Efficient intramolecular N/O-nucleophilic cyclization of 2-aryl indoles has been developed to afford the corresponding 2-aza-3-oxaindolines and 3-indolinones in 80-95% yield. The methods provided convenient access to fused imidazo[1,2-c]oxazolidinone, oxazolidine, or tetrahydro-1,3-oxazine cores under mild conditions.

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

Fe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for cyclization of 2- aminochalcones to 2- aryl-2,3- dihydroquinolin- 4(1H)- ones

Silica ferric hydrogensulfate is an efficient heterogeneous catalyst for the cyclization of 2- aminochalcones to the corresponding 2,3-dihydroquinolin- 4(1H)-ones. This intramolecular aza Michael reaction was carried out in high yields using chalcones bearing of electron donating and electron withdrawing groups. The catalyst is reusable without significant decreases in its activity after four t...

متن کامل

Fe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for cyclization of 2- aminochalcones to 2- aryl-2,3- dihydroquinolin- 4(1H)- ones

Silica ferric hydrogensulfate is an efficient heterogeneous catalyst for the cyclization of 2- aminochalcones to the corresponding 2,3-dihydroquinolin- 4(1H)-ones. This intramolecular aza Michael reaction was carried out in high yields using chalcones bearing of electron donating and electron withdrawing groups. The catalyst is reusable without significant decreases in its activity after four t...

متن کامل

Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles.

A novel and metal-free I2-mediated intramolecular C2 amidation of indoles under mild reaction conditions is developed. This methodology affords various indole fused tetracyclic compounds, such as benzo[4,5]imidazo[1,2-a]indoles by intramolecular C2 amidation of N-aryl substituted indoles. This C2 sulfonamidative cyclization also offers convenient access to indolo[2,3-b]indoles and dihydroindolo...

متن کامل

An isonitrile-alkyne cascade to di-substituted indoles

Intramolecular tin and sulfur mediated free-radical cyclizations between an aryl isonitfile and a pendant TMSsubstituted alkyne give 2,3-disubstituted indoles from 5-exo-dig cyclization and nucleophilic trapping of the resulting indolenine intermediate. © 1999 Elsevier Science Ltd. All fights reserved. In spite of the fact that Fischer first described their synthesis some 115 years ago, 1 the g...

متن کامل

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derive...

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 22  شماره 

صفحات  -

تاریخ انتشار 2014