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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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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...
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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.
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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...
2.8K
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

7.9K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the...
7.9K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.3K
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,...
3.3K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

5.0K
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,...
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Iridium-catalyzed reductive nitro-Mannich cyclization.

Alex W Gregory1, Alan Chambers, Alison Hawkins

  • 1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 18, 2014
PubMed
Summary

A novel reductive nitro-Mannich cyclization reaction sequence efficiently synthesizes alkaloid natural-product-like structures from nitroalkyl-tethered lactams. This iridium(I)-catalyzed method achieves high yields and diastereoselectivities, demonstrated in a four-step total synthesis.

Keywords:
Mannich reactionamide activationdomino reactionsiridiumreductionsilanes

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Lactams are versatile heterocyclic compounds.
  • Accessing complex alkaloid structures remains a challenge in organic synthesis.

Purpose of the Study:

  • To develop a novel chemoselective reductive nitro-Mannich cyclization reaction sequence.
  • To synthesize alkaloid natural-product-like structures efficiently.

Main Methods:

  • Iridium(I)-catalyzed reduction of lactams to enamines.
  • Subsequent nitro-Mannich cyclization of tethered nitroalkyl functionality.
  • NMR studies and characterization of reaction intermediates to elucidate the mechanism.

Main Results:

  • Developed a new reaction sequence for nitroalkyl-tethered lactams.
  • Achieved yields up to 81% for alkaloid-like structures.
  • Demonstrated good to excellent diastereoselectivities.
  • Successfully applied the methodology to the total synthesis of (±)-epi-epiquinamide in four steps.

Conclusions:

  • The developed methodology provides direct access to important alkaloid natural-product-like structures.
  • The reaction is rapid, chemoselective, and proceeds with high stereocontrol.
  • The study offers an in-depth mechanistic understanding of the transformation.