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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.8K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.8K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

5.9K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
5.9K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

11.9K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
11.9K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

12.6K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
12.6K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.3K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.3K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

8.8K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
8.8K

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Related Experiment Video

Updated: Jun 21, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

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3-Substituted 6-Azabicyclo[3.1.1]heptanes: Nonclassical Piperidine Isosteres for Drug Discovery.

Anton V Chernykh1,2,3, Bohdan V Vashchenko1,3, Svitlana V Shishkina2,4

  • 1Enamine Ltd. (www.enamine.net), Winston Churchill Street 78, Kyiv 02094, Ukraine.

The Journal of Organic Chemistry
|July 11, 2024
PubMed
Summary

Large-scale synthesis of 6-azabicyclo[3.1.1]heptane analogs provides versatile intermediates for piperidine and tropane derivatives. These novel building blocks offer unique three-dimensional structures for drug discovery and chemical synthesis.

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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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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Piperidine and tropane scaffolds are prevalent in pharmaceuticals.
  • Efficient synthesis of novel analogs is crucial for drug discovery.
  • Existing synthetic routes may lack scalability or versatility.

Purpose of the Study:

  • To develop a scalable synthetic route for 3-substituted 6-azabicyclo[3.1.1]heptanes.
  • To produce key intermediates for piperidine and tropane analogs.
  • To explore the structural and chemical properties of these novel compounds.

Main Methods:

  • Large-scale synthesis utilizing double alkylation of malonate with azetidine derivatives.
  • Hydrolysis and decarboxylation reactions to yield key intermediates.
  • Functional group transformations to access diverse building blocks.

Main Results:

  • Successful large-scale synthesis (up to 400 g) of 6-azabicyclo[3.1.1]heptane derivatives.
  • Preparation of a common intermediate, N-Boc-6-azabicyclo[3.1.1]heptane-3,3-dicarboxylic acid.
  • Access to diastereomerically pure cis and trans isomers of N-Boc-monoprotected diamines and amino alcohols.

Conclusions:

  • A robust and scalable synthetic strategy for advanced piperidine and tropane analogs was established.
  • The synthesized 6-azabicyclo[3.1.1]heptane building blocks offer unique three-dimensional structural features.
  • These compounds serve as valuable intermediates for the development of novel pharmaceutical agents.