Structurally-defined potassium-mediated regioselective zincation of amino- and alkoxy-substituted pyridines.

نویسندگان

  • Ben Conway
  • David V Graham
  • Eva Hevia
  • Alan R Kennedy
  • Jan Klett
  • Robert E Mulvey
چکیده

The new synergic base [PMDETA.K(TMP)(Et)Zn(Et)] selectively zincates 4-(dimethylamino)pyridine at the 2-position and 4-methoxypyridine at the 3-position, to afford bimetallic potassium pyridylzinc complexes each displaying a novel, but remarkably different, structure.

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

Structurally Defined Potassium-Mediated Zincation of Pyridine and 4-R-Substituted Pyridines (R=Et, iPr, tBu, Ph, and Me2N) by Using Dialkyl–TMP–Zincate Bases

Two potassium-dialkyl-TMP-zincate bases [(pmdeta)K(mu-Et)(mu-tmp)Zn(Et)] (1) (PMDETA = N,N,N',N'',N''-pentamethyldiethylenetriamine, TMP = 2,2,6,6-tetramethylpiperidide), and [(pmdeta)K(mu-nBu)(mu-tmp)Zn(nBu)] (2), have been synthesized by a simple co-complexation procedure. Treatment of 1 with a series of substituted 4-R-pyridines (R = Me(2)N, H, Et, iPr, tBu, and Ph) gave 2-zincated products ...

متن کامل

Anti-inflammatory and analgesic activities of some newly synthesized pyridinedicarbonitrile and benzopyranopyridine derivatives.

In continuation of our search for new substituted pyridine based anti-inflammatories, reaction of 1-(2-thienyl or furanyl)-3-(2-hydroxyphenyl)-2-propen-1-ones (1) with malononitrile in alcoholic KOH solution afforded a mixture of 4-alkoxy-2-(2-thienyl or furanyl)-5H-[1]benzopyrano[3,4-c]pyridine-5-ones (2) and 2-alkoxy-4-amino-6- (2-thienyl or furanyl)-3,5-pyridinedicarbonitriles (3). Some of t...

متن کامل

Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes.

Irradiation of substituted 2-benzylidenecyclopentanone O-alkyl and O-acetyloximes in methanol provides a convenient synthesis of alkyl, alkoxy, hydroxy, acetoxy, amino, dimethylamino and benzo substituted annulated quinolines. para-Substituents yield 6-substituted-2,3-dihydro-1H-cyclopenta[b]quinolines with 8-substituted products being obtained from ortho-substituted starting materials. Reactio...

متن کامل

A regioselective synthesis of 1-haloisoquinolines via ruthenium-catalyzed cyclization of O-methylbenzohydroximoyl halides with alkynes.

A ruthenium-catalyzed highly regioselective cyclization of substituted N-methoxy benzimidoyl halides with alkynes in the presence of CsOAc (25 mol%) to give substituted 1-halo and 1-alkoxy substituted isoquinolines in good to excellent yields is described.

متن کامل

Tetrabutylammonium bromide-Cesium carbonate: new reagent system for the synthesis of substituted pyridines at room temperature

The highly substituted pyridine derivatives are found to exhibit diverse pharmacological activities. They are also emerged as potential medicinal leads in developing therapeutic agents for the treatment of various diseases. In this work, a series of 2-amino-3,5-dicarbonitrile-6-thio-pyridine derivatives have been synthesized at room temperature via one-pot, multi-component reaction of various 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:
  • Chemical communications

دوره 23  شماره 

صفحات  -

تاریخ انتشار 2008