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Related Concept Videos

Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...
Preparation of Amides01:29

Preparation of Amides

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...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

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Related Experiment Video

Updated: May 13, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Solution-phase parallel synthesis of a multisubstituted cyclic imidate library.

Saurabh Mehta1, Jesse P Waldo, Benjamin Neuenswander

  • 1Department of Chemistry, Iowa State University , Ames, Iowa 50011, United States.

ACS Combinatorial Science
|March 22, 2013
PubMed
Summary
This summary is machine-generated.

A new method enables the parallel synthesis of cyclic imidates using palladium catalysis. This approach efficiently creates diverse molecular libraries for further chemical exploration and drug discovery.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Cyclic imidates are important scaffolds in medicinal chemistry.
  • Efficient synthesis of diverse cyclic imidate libraries is crucial for drug discovery.
  • Palladium-catalyzed reactions offer powerful tools for C-C and C-N bond formation.

Purpose of the Study:

  • To develop a robust and versatile solution-phase parallel synthesis method for multisubstituted cyclic imidates.
  • To create a diverse library of 71 cyclic imidate compounds.
  • To explore the functionalization of these cyclic imidates using various palladium-catalyzed cross-coupling reactions.

Main Methods:

  • Palladium/copper-catalyzed cross-coupling of o-iodobenzamides with terminal alkynes.
  • Electrophilic cyclization of the resulting intermediates with iodine (I2).
  • Further functionalization via Suzuki-Miyaura, Sonogashira, carbonylative amidation, and Heck reactions.

Main Results:

  • Successful synthesis of a 71-member library of multisubstituted cyclic imidates.
  • Good to excellent yields for the key 3-iodomethylene-containing cyclic imidate intermediates.
  • Demonstrated versatility in further functionalization using various palladium-catalyzed cross-coupling reactions.

Conclusions:

  • The described method provides an efficient route to diverse cyclic imidate libraries.
  • This approach facilitates the exploration of novel chemical space for drug discovery.
  • The synthesized cyclic imidates serve as valuable building blocks for further chemical modifications.