Jove
Visualize
Contact Us

Related Concept Videos

Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

17.1K
Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
17.1K
Reaction Mechanisms03:06

Reaction Mechanisms

26.5K
Chemical reactions often occur in a stepwise fashion, involving two or more distinct reactions taking place in a sequence. A balanced equation indicates the reacting species and the product species, but it reveals no details about how the reaction occurs at the molecular level. The reaction mechanism (or reaction path) provides details regarding the precise, step-by-step process by which a reaction occurs.
For instance, the decomposition of ozone appears to follow a mechanism with two steps:
26.5K
Multi-Step Reactions02:31

Multi-Step Reactions

7.5K
Chemical reactions often occur in a stepwise fashion involving two or more distinct reactions taking place in a sequence. A balanced equation indicates the reacting species and the product species, but it reveals no details about how the reaction occurs at the molecular level. The reaction mechanism (or reaction path) provides details regarding the precise, step-by-step process by which a reaction occurs. Each of the steps in a reaction mechanism is called an elementary reaction. These...
7.5K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.6K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.6K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.2K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.2K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

4.1K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
4.1K

You might also read

Related Articles

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

Sort by
Same author

mRNA delivery of a class 1/4 SARS-CoV-2 neutralizing antibody protects against diverse sarbecoviruses in a lethal mouse challenge model.

Proceedings of the National Academy of Sciences of the United States of America·2026
Same author

Bridged scaffold editing of carbocycles and heterocycles.

Nature communications·2026
Same author

Bivalent mRNA booster encoding virus-like particles elicits potent polyclass receptor-binding domain antibodies in pre-vaccinated mice.

eLife·2026
Same author

Catalytic Carbonylation of Dienes to Polyamides with Hydroxylamine as the Nitrogen Source.

ACS macro letters·2026
Same author

Machine learning-based clinical decision support tool for advanced ESCC in the immunotherapy era: a multi-center study.

Cancer biology & medicine·2026
Same author

Integrating central-slice anatomy and MRF-mapped radiomics dynamics for lung adenocarcinoma subtyping.

Quantitative imaging in medicine and surgery·2026
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 Experiment Video

Updated: Sep 17, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K

Novel Mannich-Type Multicomponent Reactions: Discovery, Mechanism, and Application.

Xianjing Zhou1, Zhencheng Lai1, Jiaming Li1

  • 1Institute of Drug Discovery and Design, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.

Accounts of Chemical Research
|July 1, 2025
PubMed
Summary

This study introduces novel multicomponent reactions (MCRs) for synthesizing complex molecules, particularly enabling Mannich reactions with unactivated C-H bonds for drug discovery and natural product modification.

More Related Videos

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.7K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.3K

Related Experiment Videos

Last Updated: Sep 17, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.7K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.3K

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Methodology

Background:

  • Multicomponent reactions (MCRs) are crucial for efficient synthesis of complex molecules.
  • The Mannich reaction, a key MCR, typically involves activated C-H bonds.
  • Developing Mannich reactions for unactivated C-H bonds, especially C(sp³)-H, is challenging.

Purpose of the Study:

  • To develop novel Mannich-type multicomponent reactions involving unactivated C-H bonds.
  • To explore the application of these MCRs in scaffold evolution of natural products and drug discovery.
  • To elucidate the mechanistic pathway of the novel Mannich reactions.

Main Methods:

  • Investigated a serendipitous discovery leading to a double Mannich alkylamination.
  • Conducted mechanistic studies involving multiple Mannich, retro-Mannich, and dehydrogenation steps.
  • Developed Mannich-type MCRs utilizing benzofurans/indoles, formaldehyde, and alkylamine hydrochlorides.

Main Results:

  • Achieved unprecedented alkylamination in both C(sp²)-H and unactivated benzylic C(sp³)-H bonds.
  • Successfully synthesized piperidine-fused benzofurans/indoles and indole-fused seven-membered heterocycles.
  • Demonstrated broad compatibility with medicinally relevant functionalities and successful scaffold evolution of tanshinones.

Conclusions:

  • Developed a powerful synthetic toolbox for scaffold evolution of natural products and drug discovery.
  • Pioneered chemical evolution of tanshinones, leading to potent NLRP3 inflammasome inhibitors and effective ALI treatments.
  • Generated promising drug candidates, including novel HDAC, P-gp, and STAT3 inhibitors, highlighting the MCRs' therapeutic potential.