Activation of the Carboxylic Acids by Anhydride Formation with N-Acyl-N-Alkyl Carbamic Acid

نویسنده

  • Branimir Gaspert
چکیده

The mixed anhydrides with N-acyl carbamic acid (IV) were prepared by the reaction of carboxylic acids (Ill) with N-chlorocarbonyl lactams (Ila) or sec. amides (lib). Decarboxylation of IV yielded N-acyl lactams (VI), while symmetrical anhydrides (VII) were obtained by the side reaction of IV with carboxylic acids (III). Aminolysis of IV yielded carboxylic acid amides (IX) in high yield and purity. IVb was used in the preparation of aminosubstituted beta-lactam antibiotics (XII), as a new way of activating N-protected phenylglycine (lllg), during acylation of 6-APA or 7-ADCA (XI).

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

Mixed Anhydrides of Penicillinic and Cephalosporinic Acids with N - Acyl Carbamic Aci ~ 1

Mixed anhydrides with penicillinic acids (III) were unstable and gave N-acyl, amides IV. Only III with butyrolactam was stable and reacted with alcohols to give esters V. All anhydrides with cephalosporinic acids (VIlI) yielded symmetric anhydrides IX. Alcoholysis of IX gave cephalosporinic ester X, while aminolysis yielded amide. Formation of postulated isomeric mixed anhydride with O-imino ca...

متن کامل

Zirconium Dodecylphosphonate: Selective and Constructive Catalyst for Preparation of 2-Alkyl Benzoxazoles from Aliphatic Carboxylic Acids

In this study, zirconium dodecylphosphonate was synthesized by the reported method in scientific literature. 2-Alkylbenzoxazoles were prepared from aliphatic carboxylic acids and 2-aminophenol in the presence of this catalyst under solvent-free conditions at 100°C. Their structures were recognized by IR, 1H NMR, and 13C NMR. Then, we used aromatic carboxylic acids in t...

متن کامل

Manganese (III)-Bis(salicylaldehyde)-4-Methyl-1,2-Phenylenediimine (Mn-BSMP) as an Inexpensive N2O2 Type Schiff Base Catalyst for Oxidative Decarboxylation of Carboxylic Acids with (n-Bu4NIO4) in the Presence of Imidazol

In this study, bis(salicylaldehyde)-4-methyl-1,2-phenylenediimine (BSMP) as a Schiff base ligand of N2O2-type and its Mn and Fe complex as M-BSMP catalyst were synthesized and characterized by UV-Vis, IR spectroscopy and elemental analysis. The efficiency of Fe- and Mn-BSMP catalysts was evaluated in the oxidative decarboxylation of arylacetic acids with tetra...

متن کامل

Regioselective ortho-arylation and alkenylation of N-alkyl benzamides with boronic acids via ruthenium-catalyzed C-H bond activation: an easy route to fluorenones synthesis.

A highly regioselective ruthenium-catalyzed ortho-arylation of substituted N-alkyl benzamides with aromatic boronic acids in the presence of [{RuCl(2)(p-cymene)}(2)], AgSbF(6), and Ag(2)O is described. Further, ortho-arylated N-alkyl benzamides were converted into fluorenones in the presence of trifluoroacetic anhydride and HCl.

متن کامل

One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde

The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were comp...

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 2018