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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.0K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.0K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.7K
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...
4.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.7K
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...
4.7K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.2K
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.
3.2K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.6K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.6K
Dehydration Synthesis01:15

Dehydration Synthesis

150.5K
Overview
Dehydration synthesis (also called a condensation reaction) is the chemical process in which two molecules covalently link together to form a new molecule, along with the release of a water molecule. Many physiologically important compounds form by dehydration synthesis reactions, such as complex carbohydrates, proteins, DNA, and RNA.
Synthesis of carbohydrates
Sugar molecules are covalently linked together by dehydration synthesis. During the reaction, the hydroxyl (-OH) group from...
150.5K

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Updated: Feb 13, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

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Isoselenocyanates: Synthesis and Their Use for Preparing Selenium-Based Heterocycles.

Raul Neri1, Stefan H Bossmann1,2

  • 1Kansas State University, Department of Chemistry, Manhattan, KS 66506-0401, USA.

Synthesis
|February 12, 2026
PubMed
Summary
This summary is machine-generated.

Isoselenocyanates (ISCs) show promise as cancer and infectious disease treatments, offering greater potency than isothiocyanates (ITCs). This review explores ISC synthesis and their use in creating novel, biologically active selenium-containing heterocycles.

Keywords:
iodine-promoted cyclizationisoselenocyanidesmulticomponent reactionsselenium heterocyclesselenourea

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Chemical Biology

Background:

  • Isoselenocyanates (ISCs) are organoselenium compounds with significant therapeutic potential.
  • They exhibit enhanced biological activity, including greater cytotoxicity against cancer cells compared to isothiocyanates (ITCs).
  • ISCs are crucial intermediates for synthesizing biologically active selenium-containing heterocycles.

Purpose of the Study:

  • To review classical and recent synthetic methods for isoselenocyanates (ISCs).
  • To highlight recent synthetic advancements utilizing ISCs for novel selenium heterocycle preparation.
  • To address challenges in synthesizing selenium heterocycles and showcase ISCs as versatile reagents.

Main Methods:

  • Review of established and contemporary synthetic routes for ISCs.
  • Analysis of synthetic strategies employing ISCs to construct selenium-containing heterocycles.
  • Discussion of the chemical properties and reactivity of ISCs in organic synthesis.

Main Results:

  • ISCs are increasingly accessible through improved synthetic methodologies.
  • ISCs serve as effective and versatile precursors for a diverse range of selenium heterocycles.
  • The use of ISCs circumvents difficulties associated with toxic selenium reagents in heterocycle synthesis.

Conclusions:

  • Isoselenocyanates are valuable building blocks in organoselenium chemistry.
  • Their application facilitates the synthesis of novel, biologically active selenium heterocycles.
  • ISCs represent a promising avenue for developing new chemotherapeutic and chemopreventative agents.