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Related Concept Videos

Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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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,...
2.4K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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.
2.8K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.5K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.5K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
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...
3.9K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.7K
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,...
3.7K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

4.8K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
4.8K

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Sequential Nitrile Amidination-Reduction as a Straightforward Procedure to Selective Linear Polyamine Preparation.

Antonio Peñas-Sanjuán1, Jose J Chica-Armenteros1, Rubén Cruz-Sánchez1

  • 1Departamento de Química Inorgánica y Orgánica. Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain.

The Journal of Organic Chemistry
|November 25, 2023
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A new two-step method efficiently synthesizes linear polyamines using cyclic amidine chemistry. This approach avoids harsh conditions, protective groups, and complex workups for straightforward polyamine synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Polymer Science

Background:

  • Linear polyamines are crucial building blocks in various chemical applications.
  • Existing synthesis methods often involve harsh conditions, multiple protection/deprotection steps, or tedious purification.
  • Development of efficient and robust synthetic routes for polyamines remains an active area of research.

Purpose of the Study:

  • To develop a straightforward and efficient strategy for synthesizing linear saturated polyamines.
  • To utilize cyclic amidine chemistry for polyamine backbone construction.
  • To establish a robust methodology avoiding protective groups and harsh conditions.

Main Methods:

  • Synthesis of 5- and 6-membered cyclic amidines from nitrile precursors.
  • Chemoselective reductive-opening of cyclic amidines using borane-dimethyl sulfide complex.
  • A two-step procedure for constructing linear polyamine skeletons.

Main Results:

  • Efficient synthesis of linear polyamines containing 1,2-diaminoethane and/or 1,3-diaminopropane fragments.
  • Demonstration of the utility of cyclic amidine chemistry in polyamine synthesis.
  • Successful application of the two-step procedure under mild, non-harsh conditions.

Conclusions:

  • The developed strategy offers an efficient and robust method for linear polyamine synthesis.
  • The use of cyclic amidines and borane-dimethyl sulfide provides a protective-group-free route.
  • This methodology simplifies polyamine synthesis, reducing workup complexity and harsh reaction conditions.