A diastereoselective synthesis of pyrano fused coumarins via organocatalytic three-component reaction.

نویسندگان

  • Somayeh Ahadi
  • Mahdi Zolghadr
  • Hamid Reza Khavasi
  • Ayoob Bazgir
چکیده

A new method for the synthesis of pyran fused coumarins by 3-bromo-4-hydroxycoumarins as cyclic α-halo ketones based on an organocatalyst assisted three-component tandem reaction is investigated. To the best of our knowledge, cyclic α-halo ketones have not yet been used for the synthesis of pyran fused coumarins.

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

Silica Sodium Carbonate as an Effective and Reusable Catalyst for the Three-Component Synthesis of Pyrano Coumarins

Silica sodium carbonate (SSC) has been used as a valuable silica-supported catalyst for the preparation of a range of known and novel pyrano coumarins via the three-component reactions of aryl aldehydes, active methylene compound (malononitrile or ethyl cyanoacetate), and hydroxycoumarin (5,7-dihydroxy-4-substituted coumarins or 4-hydroxycoumarin). The heterogeneous catalyst showed much the sam...

متن کامل

An efficient domino reaction in ionic liquid: synthesis and biological evaluation of some pyrano- and thiopyrano-fused heterocycles.

An improved domino/Knoevenagel-hetero-Diels-Alder reaction of two new aldehyde substrates; 7-olefinoxy-coumarin-8-carbaldehyde and 2-alkensulfanyl-quinoline-3-carbaldehyde, with pyrazolones was studied in ionic liquid triethylammonium acetate (TEAA), affording a series of pyrazolopyran annulated-pyrano-fused coumarins, and thiopyrano-fused quinolones. Besides acting as catalyst, since no additi...

متن کامل

A Convenient Base-Mediated Diastereoselective Synthesis of 2-Oxo-N,4,6-triarylcyclohex-3-enecarboxamides via Claisen-Schmidt Condensation

Sodium acetate catalyzed the multi-component reaction of acetophenone, aromatic aldehydes, and acetoacetanilide in the water-ethanol mixture (1:1) at ambient temperature via Claisen-Schmidt condensation results in the formation of highly substituted cyclohexenones in 89–98% yields. The developed efficient catalytic approach to the substituted cyclohexenones – the promising ...

متن کامل

Diastereoselective Synthesis of Stable Phosphorus Yields by a Three-Component Reaction between Ph3P and Acetylenic Esters in the Presence of Hydrazine Derivatives

In this work, stable crystalline phosphorus yields are obtained in good yields from the 1:1:1 addition reactions between hydrazine derivatives and dialkyl acetylenedicarboxylates in the presence of triphenylphosphine at room temperature in dichloromethane. This synthetic method has merits of high yields, mild reaction conditions, and simple experimental and work-up conditions. The obtained yiel...

متن کامل

Convenient One-pot Access to Pyrano[2,3-d]pyrimidine Derivatives via a CuCl2.2H2O Catalyzed Knoevenagel-Michael Addition Reaction in Water/Ethanol Media

Convenient procedure for the synthesis of corresponding pyrano[2,3-d]pyrimidine derivatives were developed via one-pot three-component reaction of aryl aldehyde derivatives, malononitrile with barbituric acids in the presence of copper (II) chloride dihydrate (CuCl2.2H2O) as highly efficient Lewis acid catalyst. This protocol has advantages such as readily and inexpensive catalyst, high reactio...

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 11 2  شماره 

صفحات  -

تاریخ انتشار 2013