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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Preparation of 1° Amines: Azide Synthesis01:22

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Mitsunobu Reaction Using Basic Amines as Pronucleophiles.

Hai Huang1, Jun Yong Kang1

  • 1Department of Chemistry and Biochemistry, University of Nevada Las Vegas , 4505 S. Maryland Parkway, Las Vegas, Nevada 89154-4003, United States.

The Journal of Organic Chemistry
|May 31, 2017
PubMed
Summary
This summary is machine-generated.

A new N-heterocyclic phosphine-butane (NHP-butane) method expands the Mitsunobu reaction for creating C-N bonds using amine nucleophiles. This approach efficiently synthesizes pharmaceuticals like Piribedil and Cinnarizine.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The Mitsunobu reaction is a versatile tool for forming C-O, C-N, and C-S bonds.
  • Expanding the scope of the Mitsunobu reaction to diverse nucleophiles remains an active area of research.

Purpose of the Study:

  • To develop a novel protocol for the Mitsunobu reaction utilizing N-heterocyclic phosphine-butane (NHP-butane).
  • To enable the formation of carbon-nitrogen (C-N) bonds using amine nucleophiles.

Main Methods:

  • A new NHP-butane reagent was employed in the Mitsunobu reaction.
  • Aliphatic alcohols, benzyl alcohols, benzoic acids, phenols, thiophenol, and secondary sulfonamides were used as substrates.
  • The reaction was applied to the synthesis of C-N bond-containing pharmaceuticals.

Main Results:

  • The developed protocol successfully formed C-N bonds from amine nucleophiles and alcohols.
  • Yields for various products including esters, ethers, thioethers, and tertiary sulfonamides ranged from 43-93%.
  • The pharmaceuticals Piribedil and Cinnarizine were synthesized in a single step from commercial amines.

Conclusions:

  • NHP-butane is an effective reagent for extending the scope of the Mitsunobu reaction to amine nucleophiles.
  • This method provides a facile route for synthesizing C-N bonds and related compounds, including important pharmaceuticals.