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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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.
3.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.6K
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...
9.6K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.1K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.1K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.9K

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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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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Functionalized 2,2'-Bipyrroles: Building Blocks for Pyrrolic Macrocycles.

Gonzalo Anguera1,2, James T Brewster1, David Sánchez-García2

  • 1Department of Chemistry the University of Texas at Austin, A5300 Austin, 78712-1224 Texas, United States.

Macroheterocycles
|November 26, 2019
PubMed
Summary

This review covers key methods for synthesizing 2,2'-bipyrroles, essential for creating macrocycles and natural products like prodigiosines. These compounds are vital for building porphyrinoids and critical structural elements.

Keywords:
2,2’-Bipyrrolesexpanded porphyrinsmacrocyclesoligopyrroles

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • 2,2'-Bipyrroles are fundamental units in organic synthesis.
  • They are precursors to complex natural products, including prodigiosines.
  • Their structure is crucial for developing novel macrocycles.

Purpose of the Study:

  • To review essential synthetic methodologies for N-unsubstituted 2,2 '-bipyrroles.
  • To highlight the significance of 2,2 '-bipyrroles as building blocks.
  • To discuss their role in synthesizing porphyrinoids and related structures.

Main Methods:

  • Literature review of established synthetic routes.
  • Analysis of key reactions for 2,2 '-bipyrrole formation.
  • Examination of their application in constructing larger molecular frameworks.

Main Results:

  • Compilation of the most effective and widely used methods for 2,2 '-bipyrrole synthesis.
  • Demonstration of their versatility as synthons.
  • Identification of structure-property relationships in derived porphyrinoids.

Conclusions:

  • N-unsubstituted 2,2 '-bipyrroles are versatile and indispensable building blocks.
  • Efficient synthetic strategies are crucial for accessing these compounds.
  • Their application extends to the development of advanced materials and pharmaceuticals.