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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Nitrosation of Enols01:19

Nitrosation of Enols

10.4K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition.

Rachel C Furnival1, Rungroj Saruengkhanphasit1, Heather E Holberry1

  • 1Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK. i.coldham@sheffield.ac.uk.

Organic & Biomolecular Chemistry
|November 8, 2016
PubMed
Summary

Simple haloaldehydes react with hydroxylamine and activated dipolarophiles to form cyclic heterocyclic compounds. This cascade reaction efficiently synthesizes pyrrolizinones, indolizinones, and pyrrolo[2,1-a]isoquinolinones, including natural products.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Heterocyclic Chemistry

Background:

  • Cascade reactions offer efficient synthetic routes to complex molecules.
  • Multi-component reactions (MCRs) are valuable for rapid assembly of diverse chemical structures.
  • Heterocyclic compounds are prevalent in pharmaceuticals and natural products.

Purpose of the Study:

  • To explore a novel multi-component cascade reaction for synthesizing heterocyclic compounds.
  • To develop an efficient method for preparing pyrrolizinones, indolizinones, and pyrrolo[2,1-a]isoquinolinones.
  • To demonstrate the utility of this chemistry through the synthesis of natural products.

Main Methods:

  • Condensation of haloaldehydes with hydroxylamine to form oximes.
  • Cyclization of oximes with halide displacement to generate nitrones.
  • In situ intermolecular 1,3-dipolar cycloaddition of nitrones with activated dipolarophiles.
  • Reductive cleavage of cycloadducts to yield lactam products.

Main Results:

  • A novel cascade reaction sequence was established, starting from simple haloaldehydes.
  • Isoxazolidines were formed as key intermediates via 1,3-dipolar cycloaddition.
  • Pyrrolizinones, indolizinones, and pyrrolo[2,1-a]isoquinolinones were synthesized efficiently.
  • The synthesis of macronecine and petasinecine was demonstrated.

Conclusions:

  • This multi-component reaction provides a facile and versatile route to complex nitrogen-containing heterocycles.
  • The developed methodology is applicable to the synthesis of biologically relevant molecules and natural products.
  • The cascade approach offers advantages in terms of step economy and efficiency.