Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Regioselective Formation of Enolates

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Fluorinated Guanidino-Polyamine Conjugates with Ribonuclease Activity - Toward a Therapeutic Tool for Multi-Drug Therapy.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025

Same author

Fluorinated Redox-Responsive Cross-Linked Poly(amidoamine) G2 as Smart Theranostic Dendrimers.

Biomacromolecules·2025

Same author

Fine-Tuned "Click" Functionalization of PAMAM Dendrimers with a Linear Fluorinated Guanidino Linker: Synthesis, Characterization, and Applications.

Bioconjugate chemistry·2024

Same author

Dual Antibiotic Approach: Synthesis and Antibacterial Activity of Antibiotic-Antimicrobial Peptide Conjugates.

Antibiotics (Basel, Switzerland)·2024

Same author

Fluorinated PAMAM-Arginine Carrier Prodrugs for pH-Sensitive Sustained Ibuprofen Delivery.

Pharmaceutical research·2024

Same author

Turn-Mimic Hydantoin-Based Loops Constructed by a Sequential Multicomponent Reaction.

The Journal of organic chemistry·2023

Search research articles

Related Experiment Video

Updated: May 17, 2026

Synthesis of a Water-soluble Metal–Organic Complex Array

Synthesis of a Water-soluble Metal–Organic Complex Array

Published on: October 8, 2016

Regioselective multicomponent sequential synthesis of hydantoins.

Francesca Olimpieri¹, Maria Cristina Bellucci, Tommaso Marcelli

¹Department of Chemistry, Materials and Chemical Engineering Giulio Natta, Politecnico di Milano, via Mancinelli 7, 20131 Milano, Italy.

Organic & Biomolecular Chemistry

|October 19, 2012

Summary

Researchers developed a green, one-pot synthesis for substituted hydantoins using accessible starting materials. This method efficiently produces spiro-hydantoins, valuable in medicinal chemistry and drug discovery.

More Related Videos

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Related Experiment Videos

Last Updated: May 17, 2026

Synthesis of a Water-soluble Metal–Organic Complex Array

Synthesis of a Water-soluble Metal–Organic Complex Array

Published on: October 8, 2016

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Area of Science:

Organic Synthesis
Medicinal Chemistry
Green Chemistry

Background:

Heterocyclic compounds are crucial scaffolds in drug discovery.
Developing efficient and environmentally friendly synthesis methods is a key research area.
Hydantoins, a class of heterocycles, show significant biological activity.

Purpose of the Study:

To develop a novel, practical, and green synthetic route for substituted hydantoins.
To establish a one-pot, three-component sequential procedure for hydantoin synthesis.
To facilitate the synthesis of spiro-hydantoins for medicinal chemistry applications.

Main Methods:

A one-pot, three-component sequential reaction was employed.
Readily accessible starting materials including azides, iso(thio)cyanates, and α-halo-acetic carboxylic acids were used.
The synthesis was performed under very mild conditions.

Main Results:

Diversely 1,3,5- and 1,3,5,5-substituted hydantoins were synthesized in high yields.
The methodology proved particularly effective for generating spiro-hydantoins.
The reaction conditions were mild and the starting materials were easily accessible.

Conclusions:

A convenient and green method for synthesizing substituted hydantoins has been established.
The developed procedure is highly efficient for producing spiro-hydantoins, important bioactive compounds.
This approach offers a valuable tool for drug discovery and medicinal chemistry research.