A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

نویسندگان

  • Raoni S B Gonçalves
  • Michael Dos Santos
  • Guillaume Bernadat
  • Danièle Bonnet-Delpon
  • Benoit Crousse
چکیده

Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The 3-trifluoromethyl-2-isoxazolines were ring-opened with NaBH4 and NiCl2 to yield the corresponding trifluoromethylated γ-amino alcohols.

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

Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones.

A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and...

متن کامل

Synthesis of 4-(trifluoromethyl) coumarins using nano sulfated-titania as solid acid catalyst under solvent-free conditions

Nano sulfated titania was tested as solid acid heterogeneous catalyst for the synthesis of 4-(Trifluoromethyl) coumarin and coumarin derivatives under solvent-free condition. Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents.  This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. The prepared sulfated titania s...

متن کامل

Synthesis of 4-(trifluoromethyl) coumarins using nano sulfated-titania as solid acid catalyst under solvent-free conditions

Nano sulfated titania was tested as solid acid heterogeneous catalyst for the synthesis of 4-(Trifluoromethyl) coumarin and coumarin derivatives under solvent-free condition. Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents.  This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. The prepared sulfated titania s...

متن کامل

Synthesis of Some New Azo Disperse Dyes and Investigation of Their Solvatochromic Effect

The synthesis and properties of new monoazo dyes derived from the diazonium salts of paminobenzoic acid, 3-trifluoromethyl aniline , 4-trifluoromethyl aniline are considered .Theprepared compounds were characterized by UV-Visible , FT-IR and H NMR spectroscopictechniques . The effect of varying solvent upon the absorption ability of p-amino benzoic acidcoupled with 4,4 —diethyl aniline , anilin...

متن کامل

General pathway for a convenient one-pot synthesis of trifluoromethyl-containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and fused cycloalkane analogues.

A convenient and general method for the synthesis in 26-73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF₃C(O)CH=C(R¹)OR, where R¹ = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NO₂Ph, 2-furyl, 2-thienyl and R = Me, Et] with 2,6-diaminopyridine (2,6-DAP), unde...

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:

دوره 9  شماره 

صفحات  -

تاریخ انتشار 2013