Synthesis of 3,3-disubstituted-2,3-dihydroazanaphthoquinones via simultaneous alkyne oxidation and nitrile hydration of ortho-alkynylarenenitriles.

نویسندگان

  • Karuppusamy Sakthivel
  • Kannupal Srinivasan
چکیده

o-Alkynylarenenitriles when heated with Pd(OAc)2/H2O/(±)-CSA in DMSO undergo simultaneous alkyne oxidation and nitrile hydration to give 3-aryl-3-hydroxy-2,3-dihydroazanaphthoquinones. Upon treatment with (±)-CSA, these compounds form 3-arylazanaphthoquinones in situ, which add to electron-rich aromatics and terminal alkene/alkyne to afford 3,3-disubstituted-2,3-dihydroazanaphthoquinones.

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

SBA-15-supported-dithizone-copper(I): An efficient heterogeneous catalyst for synthesis of 1,4-disubstituted 1,2,3-triazoles in water

In this work, the SBA-15-supported dithizone-copper(I) [SBA-15-dtz–Cu(I)] complex as a new heterogeneous catalyst is prepared for the first time. The catalyst prepared is characterized by the FT-IR spectroscopy, SEM, and ICP techniques. This reusable heterogeneous catalyst can be used in the click reactions for the green and facile synthesis of 1,4-disubstituted 1,2,3-triazolesvia a on...

متن کامل

Synthesis of functionalized aryl-alkenes catalyzed by CN-ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime under microwave irradiation

A new dimeric orthopalladated complex was synthesized via reaction of 2,3-dimethoxy benzaldehyde oxime with palladium chloride and lithium chloride in methanol as solvent and sodium acetate as base at room temperature. The catalytic activity of this dimeric [Pd{C6H2(-CH=NOH)-(OMe)2-2,3}(µ-Cl)]2 complex as an efficient, air, and moisture tolerant catalyst was investigated in Mizoroki–Heck cross ...

متن کامل

Synthesis of functionalized aryl-alkenes catalyzed by CN-ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime under microwave irradiation

A new dimeric orthopalladated complex was synthesized via reaction of 2,3-dimethoxy benzaldehyde oxime with palladium chloride and lithium chloride in methanol as solvent and sodium acetate as base at room temperature. The catalytic activity of this dimeric [Pd{C6H2(-CH=NOH)-(OMe)2-2,3}(µ-Cl)]2 complex as an efficient, air, and moisture tolerant catalyst was investigated in Mizoroki–Heck cross ...

متن کامل

Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.

Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes a...

متن کامل

Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes.

Treatment of oximes with hypervalent iodine leads to substituted isoxazoles via rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure mild enough to prepare a range of nucleoside and peptide conjugates. Exceptionally high reaction rates were found for the formation of 3,4,5-...

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 33  شماره 

صفحات  -

تاریخ انتشار 2014