1,3-Disulfonic Acid Imidazolium Trifluoroacetate as a Highly Efficient and Dual-Functional Catalyst for the Pseudo Five-Component Reaction of Phenylhydrazine with Ethyl Acetoacetate and Arylaldehydes

نویسندگان

  • Abdolkarim Zare Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran
  • Mostafa Karami Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran
چکیده مقاله:

Ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) has been exploited as a highly efficient catalyst for the one-pot pseudo five-component reaction of phenylhydrazine (2 eq.) with ethyl acetoacetate (2 eq.) and arylaldehydes (1 eq.) in ethanol (reflux conditions). In this reaction, 4,4′‐(arylmethylene)‐bis(3‐methyl‐1‐phenyl‐1H‐ pyrazol‐5‐ol)s have been obtained in high yields and relatively short reaction times. High efficacy of [Dsim][TFA] can attributed to dual-functionality (possessing three acidic and one basic sites). A plausible and attractive mechanism based on dual-functionality of the catalyst has been proposed.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

1,3-Disulfonic acid imidazolium hydrogen sulfate {[Dsim]HSO4} as a highly efficient, recyclable and green catalyst for the preparation of α,α´-bis(arylidene)cycloalkanones

A highly efficient and simple method for the preparation of α,α´-bis(arylidene)cycloalkanones under solvent-free conditions has been developed. The crossed-aldol condensation of cycloalkanones (1 eq.) with arylaldehydes (2 eq.) in the presence of 2.5 mol% of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate {[Dsim]HSO4} afforded the title compounds in high yields and short reaction ...

متن کامل

Preparation, characterization and the use of sulfonic acid-functionalized phthalimide (SFP) as a highly efficient and green catalyst for the condensation of arylaldehydes with 2-naphthol

Phthalimide was reacted with chlorosulfonic acid to give sulfonic acid-functionalized phthalimide (SFP), which characterized by 1H NMR, 13C NMR, FT-IR, XRD (X-ray diffraction), SEM (scanning electron microscopy), EDX (energy-dispersive X-ray), mass, TG (thermogravimetry) and DTG (derivative thermal gravimetry) spectra. Afterward, its catalytic activity was examined for the condensation of aryla...

متن کامل

Preparation, characterization and the use of sulfonic acid-functionalized phthalimide (SFP) as a highly efficient and green catalyst for the condensation of arylaldehydes with 2-naphthol

Phthalimide was reacted with chlorosulfonic acid to give sulfonic acid-functionalized phthalimide (SFP), which characterized by 1H NMR, 13C NMR, FT-IR, XRD (X-ray diffraction), SEM (scanning electron microscopy), EDX (energy-dispersive X-ray), mass, TG (thermogravimetry) and DTG (derivative thermal gravimetry) spectra. Afterward, its catalytic activity was examined for the condensation of aryla...

متن کامل

Trichloroacetic Acid as an Efficient Catalyst for One-pot Synthesis of Highly Functionalized Piperidines via multi-component Reaction

Trichloroacetic Acid (TCA) was used as an efficient catalyst for the synthesis of highly functionalized piperidines via a one-pot five-component reaction of aromatic amines, aromatic aldehydes and β-keto esters in MeOH at room temperature. The remarkable advantages offered by this method are good yields, simple procedure, short reaction times, no need to column chromatography and an easy wo...

متن کامل

1,3-disulfonic acid imidazolium hydrogen sulfate {[dsim]hso4} as a highly efficient, recyclable and green catalyst for the preparation of α,α´-bis(arylidene)cycloalkanones

a highly efficient and simple method for the preparation of α,α´-bis(arylidene)cycloalkanones under solvent-free conditions has been developed. the crossed-aldol condensation of cycloalkanones (1 eq.) with arylaldehydes (2 eq.) in the presence of 2.5 mol% of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate {[dsim]hso4} afforded the title compounds in high yields and short reaction ...

متن کامل

منابع من

با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ذخیره در منابع من قبلا به منابع من ذحیره شده

{@ msg_add @}


عنوان ژورنال

دوره 4  شماره 2

صفحات  174- 181

تاریخ انتشار 2018-06-01

با دنبال کردن یک ژورنال هنگامی که شماره جدید این ژورنال منتشر می شود به شما از طریق ایمیل اطلاع داده می شود.

میزبانی شده توسط پلتفرم ابری doprax.com

copyright © 2015-2023