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

Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.9K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.9K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

11.0K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
11.0K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

16.8K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
16.8K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

3.6K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.6K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.2K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.2K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.7K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.7K

You might also read

Related Articles

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

Sort by
Same author

Activating lattice oxygen in metal oxyhydroxides as durable electrodes for industrial-scale seawater splitting.

Nature communications·2026
Same author

Water Radiolysis Enables CO<sub>2</sub>-Activated Radical Recycling of Spent Lithium-Ion Cathodes.

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

Inhibition of aerobic glycolysis suppresses ferroptosis via activation of the AMPK-FoxO3a pathway in epileptic rats.

Molecular biology reports·2026
Same author

Causal relationship between autoimmune diseases and iron deficiency anemia: a two-sample mendelian randomization study.

Scientific reports·2026
Same author

Synthesis of 4H-phase high-entropy alloys for electrocatalysis.

Nature materials·2026
Same author

Unraveling the oncogenic and immunomodulatory roles of GINS1: a systematic pan-cancer study.

Cancer cell international·2026

Related Experiment Video

Updated: Oct 21, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

10.0K

A Bridge to Alkaloid Synthesis.

Li Zhai1,2, Ye Tang2, Yan Zhang2

  • 1Shanghai University of Traditional Chinese Medicine, 1200 Cailun Road, Shanghai, 201203, PR China.

Chemical Record (New York, N.Y.)
|September 2, 2021
PubMed
Summary
This summary is machine-generated.

Researchers developed new synthetic methods for creating complex bridged alkaloids, crucial for drug discovery. These novel strategies, including nitroso-ene and aza-Wacker cyclizations, yield important biologically active compounds.

Keywords:
Mannichalkaloidaza-Wackernitroso-enetotal synthesis

More Related Videos

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
09:04

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

10.8K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.0K

Related Experiment Videos

Last Updated: Oct 21, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

10.0K
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
09:04

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

10.8K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.0K

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Structurally rigid molecules with chiral complexity enhance drug target interactions.
  • Bridged alkaloids are biologically significant natural products with complex architectures.
  • Novel synthetic strategies are needed for efficient alkaloid synthesis.

Purpose of the Study:

  • To develop novel synthetic methods for constructing biologically significant bridged alkaloids.
  • To explore the application of nitroso-ene and aza-Wacker cyclizations in alkaloid synthesis.
  • To investigate the chemical reactivity and selectivity of key functional groups in these reactions.

Main Methods:

  • Application of nitroso-ene cyclization for bridged alkaloid synthesis.
  • Utilisation of aza-Wacker cyclization for bridged alkaloid construction.
  • Mechanistic investigations including computational calculations and deuterated experiments.

Main Results:

  • Successful synthesis of bridged alkaloids including hosieine A, kopsone, melinonine-E, and strychnoxanthine.
  • First-time application of nitroso-ene and aza-Wacker cyclizations to construct bridged alkaloids.
  • Gained insights into reaction mechanisms, chemical reactivity, and selectivity.

Conclusions:

  • Nitroso-ene and aza-Wacker cyclizations are effective novel methods for synthesizing complex bridged alkaloids.
  • These methods provide viable strategies for accessing biologically important natural products.
  • Mechanistic studies enhance the development of robust and selective synthetic routes.