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Preparation of Amides01:29

Preparation of Amides

3.7K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.7K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.2K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.2K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.3K
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...
4.3K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.1K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.1K
Indicators02:39

Indicators

54.0K
Certain organic substances change color in dilute solution when the hydronium ion concentration reaches a particular value. For example, phenolphthalein is a colorless substance in any aqueous solution with a hydronium ion concentration greater than 5.0 × 10−9 M (pH < 8.3). In more basic solutions where the hydronium ion concentration is less than 5.0 × 10−9 M (pH > 8.3), it is red or pink. Substances such as phenolphthalein, which can be used to determine the pH of a solution, are...
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Synthetic studies toward inducamide C.

Ardalan A Nabi1, Lydia M Scott1, Daniel P Furkert1

  • 1School of Chemical Sciences, University of Auckland, Auckland, New Zealand. j.sperry@auckland.ac.nz.

Organic & Biomolecular Chemistry
|December 14, 2020
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Summary

The natural product inducamide C, proposed to have a rare benzoxazepine ring, is unstable and may require structural revision. Synthetic attempts and computational studies reveal a tendency to form an isomeric oxepanoindole instead.

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Area of Science:

  • Natural product chemistry
  • Organic synthesis
  • Computational chemistry

Background:

  • Inducamide C is a natural product alkaloid.
  • The proposed structure of inducamide C features a rare benzoxazepine ring.

Purpose of the Study:

  • To investigate the stability of the proposed benzoxazepine ring in inducamide C.
  • To explore synthetic routes towards inducamide C.
  • To determine if structural revision of inducamide C is necessary.

Main Methods:

  • First-generation synthetic approach involving cyclization of 4-hydroxyinducamide A.
  • Second-generation synthetic approach involving dealkylation of O-isopropylinducamide C.
  • Computational studies to validate reaction pathways and product formation.

Main Results:

  • Attempts to synthesize the benzoxazepine ring resulted in the formation of a regioisomeric oxepanoindole.
  • The 4-hydroxyindole moiety preferentially cyclized over the chlorosalicylic acid moiety.
  • Rearrangement of the proposed inducamide C structure also yielded the oxepanoindole.
  • Computational studies confirmed the preferential formation of oxepanoindole and identified lactone susceptibility to nucleophilic attack.

Conclusions:

  • The benzoxazepine ring in inducamide C is unstable and prone to rearrangement.
  • Structural revision of inducamide C may be necessary due to its instability.
  • The synthetic and computational data support the instability or need for revision of inducamide C's proposed structure.