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Preparation of Nitriles01:12

Preparation of Nitriles

2.8K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.9K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
4.9K
Nitrosation of Enols01:19

Nitrosation of Enols

10.7K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
10.7K
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

6.6K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
6.6K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

5.5K
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
5.5K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.2K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.2K

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Development of variously functionalized nitrile oxides.

Haruyasu Asahara1, Keita Arikiyo2, Nagatoshi Nishiwaki1

  • 1School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan ; Research Center for Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.

Beilstein Journal of Organic Chemistry
|October 2, 2015
PubMed
Summary

This study demonstrates novel chemical transformations of N-methylated amides into various functional groups like acids, esters, and ketones. These N-methyl-N-tosylcarboxamides act as versatile Weinreb amide equivalents for synthetic chemistry.

Keywords:
Weinreb amideacylnitrile oxideamideformylnitrile oxidefunctionalized nitrile oxide

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • N-methylated amides are common functional groups in organic chemistry.
  • Developing versatile synthetic routes for amide transformations is crucial for creating diverse molecular structures.

Purpose of the Study:

  • To explore novel chemical transformations of N-methylated amides.
  • To establish N-methyl-N-tosylcarboxamides as versatile synthetic intermediates analogous to Weinreb amides.
  • To synthesize functionalized isoxazole derivatives.

Main Methods:

  • N-tosylation of N-methylated amides followed by nucleophilic substitution.
  • Treatment of N-methyl-N-tosylcarboxamides with various nucleophiles (hydroxide, alkoxide, amine, Grignard reagents, diisobutylaluminium hydride).
  • Cycloaddition reaction of ethynylbenzene and N-methylcarbamoylnitrile oxide.

Main Results:

  • Successful conversion of amide functions to carboxylic acids, esters, amides, aldehydes, and ketones.
  • Demonstration that N-methyl-N-tosylcarboxamides mimic the reactivity of Weinreb amides.
  • Synthesis of 3-functionalized isoxazole derivatives from N-methyl-5-phenylisoxazole-3-carboxamide.
  • Nitrile oxide served as a precursor for various functional groups.

Conclusions:

  • N-methyl-N-tosylcarboxamides provide a flexible platform for synthesizing diverse organic compounds.
  • The methodology offers a new route to functionalized isoxazoles and related structures.
  • This work expands the synthetic utility of N-methylated amides in organic synthesis.