Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.2K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.2K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.2K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.2K
Structure of Amines01:19

Structure of Amines

2.6K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
2.6K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

4.9K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
4.9K

You might also read

Related Articles

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

Sort by
Same author

Direct access to 2-imidazolines from unactivated alkenes.

Chemical science·2026
Same author

C═C/N═O Metathesis Enables Oxidative Decarboxylation.

Journal of the American Chemical Society·2026
Same author

Ring-opening decarbonylative C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-electrophile coupling of cyclic imides with unactivated alkyl chlorides.

Chemical science·2026
Same author

A Chemoselective and Stereodivergent Platform of Heme-Nitrene Transferases to Access Chiral Aryl-β-Amino Esters and An Investigation of the Sequence-Activity Landscape.

Angewandte Chemie (International ed. in English)·2026
Same author

Late-Stage Diversification of Native Tryptophan-Containing Peptides and Peptide Drugs through Nitrogen Atom Insertion.

Journal of the American Chemical Society·2025
Same author

Kinetic, Spectroscopic, and Computational Investigation of Oxidative Aminative Alkene Cleavage Reveals an <i>N</i>-Iodonium-Iminoiodinane Pathway.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Aug 6, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K

Nitrogen atom insertion into indenes to access isoquinolines.

Patrick Finkelstein1, Julia C Reisenbauer1, Bence B Botlik1

  • 1Laboratorium für Organische Chemie, ETH Zürich Vladimir-Prelog-Weg 3, HCI 8093 Zürich Switzerland bill.morandi@org.chem.ethz.ch.

Chemical Science
|March 20, 2023
PubMed
Summary

Researchers developed a simple method to create isoquinolines by inserting nitrogen into indenes using phenyliodine(iii) diacetate and ammonium carbamate. This versatile protocol also synthesizes pyridines and enables 15N-labeled isoquinoline production.

More Related Videos

Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

12.0K
Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds
05:59

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Published on: September 27, 2024

2.1K

Related Experiment Videos

Last Updated: Aug 6, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K
Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

12.0K
Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds
05:59

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Published on: September 27, 2024

2.1K

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Heterocyclic Chemistry

Background:

  • Isoquinoline and pyridine scaffolds are prevalent in pharmaceuticals and natural products.
  • Efficient and versatile synthetic routes for these heterocycles are highly sought after.
  • Existing methods often require harsh conditions or specialized reagents.

Purpose of the Study:

  • To develop a convenient and broadly applicable protocol for nitrogen atom insertion into indenes.
  • To synthesize a diverse range of substituted isoquinolines.
  • To extend the methodology for pyridine synthesis and 15N-labeling.

Main Methods:

  • Utilized phenyliodine(iii) diacetate (PIDA) as an oxidant.
  • Employed ammonium carbamate as a nitrogen source.
  • Investigated the reaction scope with various indene derivatives and functional groups.

Main Results:

  • Successfully synthesized a wide array of isoquinolines from indenes.
  • Demonstrated tolerance for various substitution patterns and functional groups.
  • Extended the protocol to convert cyclopentadienes into pyridines.
  • Achieved facile synthesis of 15N-labeled isoquinolines using 15NH4Cl.

Conclusions:

  • The developed protocol offers a straightforward and efficient route to isoquinolines and pyridines.
  • The method's operational simplicity and broad applicability make it valuable for synthetic chemists.
  • This strategy provides access to isotopically labeled heterocycles for further studies.