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

Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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...
Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
Structure of Amines01:19

Structure of Amines

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’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

You might also read

Related Articles

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

Sort by
Same author

Advanced Synthetic Methods in Modern Medicinal Chemistry.

Journal of medicinal chemistry·2026
Same author

Development of PROTACs Targeting the Moonlighting Enzyme Nicotinamide Phosphoribosyltransferase (NAMPT) for Breast Cancer Therapy.

Journal of medicinal chemistry·2026
Same author

Expanding the Scope of PROTACs: Opportunities and Challenges in Topical Delivery.

Journal of medicinal chemistry·2025
Same author

Calcium signaling dysregulation in rheumatoid arthritis: a comparative perspective with osteoarthritis.

Autoimmunity reviews·2025
Same author

Sustainable Photocatalytic Synthesis of Glitazones via Riboflavin Tetraacetate.

The Journal of organic chemistry·2025
Same author

Integrated proteomic and targeted Next Generation Sequencing reveal relevant heterogeneity in lower-grade meningioma and ANXA3 as a new target in NF2 mutated meningiomas.

EBioMedicine·2025
Same journal

Y(OTf)<sub>3</sub>-Catalyzed Formal (3 + 2) Cycloadditions of Donor-Acceptor Cyclopropanes with KSCN under Mechanochemical Conditions.

Organic letters·2026
Same journal

Electro-Mediated Regioselective C2-Alkylation of <i>N</i>-Oxide Heteroarenes.

Organic letters·2026
Same journal

Organophosphine-Promoted Decarbynylative Hydrocarbenylation of the Carbon-Carbon Triple Bond.

Organic letters·2026
Same journal

Total Syntheses of BE-54238A and -B.

Organic letters·2026
Same journal

Visible Light-Induced <i>N</i>-Phenylbenzo[<i>c</i>]phenothiazine-Catalyzed α-C(sp<sup>3</sup>)-H Phosphonylation of Secondary Amines via Intramolecular 1,5-HAT.

Organic letters·2026
Same journal

Cobalt-Stabilized Propargylic Oxocarbenium Ions Enable Direct and Asymmetric Nickel(II) Catalyzed Aldol-Like Reactions.

Organic letters·2026
See all related articles

Related Experiment Video

Updated: Jul 2, 2026

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials
08:55

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials

Published on: June 25, 2018

A concise entry into nonsymmetrical alkyl polyamines.

Tracey Pirali1, Grazia Callipari, Emanuela Ercolano

  • 1Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche and Drug and Food Biotechnology Center, Università degli Studi del Piemonte Orientale "A. Avogadro", Via Bovio 6, 28100 Novara, Italy.

Organic Letters
|September 4, 2008
PubMed
Summary
This summary is machine-generated.

Synthesizing nonsymmetrical polyamines (PAs) is now simpler with a novel N-split Ugi reaction. This method improves efficiency and regioselectivity, paving the way for new drug discovery.

More Related Videos

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Related Experiment Videos

Last Updated: Jul 2, 2026

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials
08:55

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials

Published on: June 25, 2018

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Nonsymmetrical polyamines (PAs) synthesis is challenging due to complex procedures, poor regioselectivity, and low atom economy.
  • Existing methods for creating these molecules are often inefficient and time-consuming.

Purpose of the Study:

  • To develop an innovative and efficient synthetic protocol for nonsymmetrical polyamines.
  • To overcome the limitations of current synthetic methods for polyamines.

Main Methods:

  • A modified Ugi reaction, termed 'N-split Ugi', was employed.
  • This novel approach streamlines the synthesis of complex polyamine structures.

Main Results:

  • The N-split Ugi reaction provides a simplified and more regioselective route to nonsymmetrical polyamines.
  • The protocol demonstrates improved efficiency compared to traditional methods.

Conclusions:

  • The developed N-split Ugi reaction offers a significant advancement in the synthesis of nonsymmetrical polyamines.
  • This new method facilitates the generation of novel polyamines with potential pharmacological applications.