Ring Opening of Epoxy Fatty Esters by Nucleophile to Form the Derivatives of Substituted β-Amino Alcohol

نویسندگان

  • Himani Varshney
  • Aiman Ahmad
  • Abdul Rauf
چکیده

The nucleophilic ring opening of epoxy fatty esters was carried out using the amino-1,2,4-triazole to yield substituted derivatives of β-amino alcohol. The synthesis of the substituted beta amino alcohols has been achieved by refluxing equimolar quantities of long chain epoxy esters (epoxy fatty esters) and 4-amino-1,2,4-triazole in dichloromethane to yield following compounds, methyl 10-(4'-amino-1',2',4'-triazole)-11-hydroxy undecanoate (V), methyl 9-(4'-amino-1', 2',4'-triazole)-10-hydroxy octadecanoate (VI), methyl 9-(4'-amino-1',2',4'-triazole)-10,12-dihydroxy octadecanoate (VII), methyl 12-(4'-amino-1',2',4'-triazole)-9,13-dihydroxy octadecanoate (VIII). Epoxides of esters of fatty acids were obtained by reaction of esters of fatty acids with m-chloroperbenzoic acid. All the newly synthesized compounds were characterized by IR, H NMR, C NMR and mass spectrometry.

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

Well-controlled ring-opening polymerization of cyclic esters initiated by dialkylaluminum β-diketiminates.

A series of aluminum alkyl complexes nacnacRAlMe2 (2a-2h) bearing aliphatic N-substituted β-diketiminate ligands (nacnacRH = N,N'-dialkyl-2-amino-4-iminopent-2-enes), were prepared from the reaction of trialkyl aluminum and the corresponding β-diketimines. All these aluminum complexes were characterized by NMR, elemental analysis and HRMS spectroscopy. The molecular structures of complexes 2a, ...

متن کامل

Synthetic studies of the lichen macrolide lepranthin. Stereoselective synthesis of the diolide framework based on regioselective epoxide-opening reactions.

Stereoselective synthesis of the 16-membered diolide 27, a fully functionalized congener of lepranthin (1), is described. The requisite five asymmetric carbon centers in monomer 23 were constructed in a highly stereoselective manner by using different epoxide-opening reactions of α,β-unsaturated γ,δ-epoxy esters and epoxy alcohol derivatives as the key steps. The monomer 23 was successfully tra...

متن کامل

Synthesis and Biological Evaluation of New Tricyclic Dihydropyridine Based Derivatives on Potassium Channels

The present study reports a microwave-assisted method for the synthesis of twelve novel tricyclic 1,4-dihydropyridine derivatives in which dimethyl-substituted cyclohexane and / or tetrahydrothiophene rings are fused to the DHP ring. The structures of the compounds were confirmed by spectral methods and elemental analysis. The potassium channel opening effects of the compounds were determined o...

متن کامل

Synthesis and Biological Evaluation of New Tricyclic Dihydropyridine Based Derivatives on Potassium Channels

The present study reports a microwave-assisted method for the synthesis of twelve novel tricyclic 1,4-dihydropyridine derivatives in which dimethyl-substituted cyclohexane and / or tetrahydrothiophene rings are fused to the DHP ring. The structures of the compounds were confirmed by spectral methods and elemental analysis. The potassium channel opening effects of the compounds were determined o...

متن کامل

Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.

The rhodium-catalyzed, directed catalytic asymmetric hydroboration of γ,δ-unsaturated amides affords a direct route to chiral acyclic secondary γ-borylated carbonyl derivatives in high enantiomeric purity. In contrast to a similar β-borylated amide derivative, the γ-borylated amide undergoes Suzuki-Miyaura cross-coupling with stereoretention. The utility of the boronic ester products is further...

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   شماره 

صفحات  -

تاریخ انتشار 2013