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Preparation of Amides01:29

Preparation of Amides

3.4K
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...
3.4K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.4K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.4K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.3K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.2K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
9.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.0K
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...
2.0K
Preparation of Nitriles01:12

Preparation of Nitriles

1.9K
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...
1.9K

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics.

Gijs Koopmanschap1, Eelco Ruijter1, Romano Va Orru1

  • 1Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute of Molecules, Medicines and Systems, VU University Amsterdam, de Boelelaan 1083, 1081 HV, Amsterdam, The Netherlands.

Beilstein Journal of Organic Chemistry
|March 8, 2014
PubMed
Summary

This review explores multicomponent reactions (MCRs) for synthesizing cyclic peptide mimics. These reactions offer a streamlined approach to creating diverse and structurally constrained peptidomimetics with enhanced pharmacological properties.

Keywords:
heterocyclesisocyanidesmacrocyclesmedicinal chemistrymulticomponent reactionorganic synthesispeptidomimetics

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • Peptide mimics (peptidomimetics) offer improved pharmacological properties over natural peptides.
  • Cyclic constructs enhance receptor affinity and enforce defined secondary structures in peptides.
  • Traditional synthesis of cyclic peptidomimetics involves multiple steps, limiting structural diversity.

Purpose of the Study:

  • To review advancements in isocyanide-based multicomponent reactions (IMCRs) coupled with cyclization strategies.
  • To highlight the utility of MCRs for creating diverse cyclic peptidomimetics.
  • To showcase the synthesis of small, medium, and macrocyclic peptidomimetics.

Main Methods:

  • Utilizing multicomponent reactions (MCRs), specifically isocyanide-based MCRs (IMCRs).
  • Incorporating bifunctional substrates into IMCRs for subsequent cyclization.
  • Employing strategies like deprotection-cyclization, ring-closing metathesis, and 1,3-dipolar cycloadditions.

Main Results:

  • IMCRs enable the introduction of molecular complexity and structural diversity in a single step.
  • Sequential IMCR-cyclization strategies yield cyclic peptide mimics ranging from small rings to macrocycles.
  • This approach facilitates the fine-tuning of biological activity through structural variation.

Conclusions:

  • IMCRs combined with cyclization are powerful tools for synthesizing diverse cyclic peptidomimetics.
  • This methodology provides efficient access to constrained structures with potential therapeutic applications.
  • Developments since 2002 have expanded the scope of IMCRs for creating various cyclic peptide mimics.