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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Preparation and Reactions of Sulfides02:26

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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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...
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2.3K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Recent developments in thiochromene chemistry.

Solai Murugappan1, Pranali Vijaykumar Kuthe1, Kondapalli Venkata Gowri Chandra Sekhar2

  • 1Department of Pharmacy, Birla Institute of Technology and Science Pilani, Pilani Campus, Vidya Vihar, Pilani-333031, Rajasthan, India. murugesan@pilani.bits-pilani.ac.in.

Organic & Biomolecular Chemistry
|July 19, 2024
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Summary

This review explores the synthesis of thiochromenes, versatile sulfur-containing compounds vital for drug discovery. It details various synthetic routes, highlighting methods for creating novel thiochromene-based drug candidates.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis

Background:

  • Thiochromenes are sulfur-containing heterocyclic compounds with significant applications in drug discovery.
  • These scaffolds are utilized in developing agents for anticancer, anti-HIV, antioxidant, and antimicrobial purposes.
  • The synthesis of thiochromenes is less explored compared to their oxygen analogs.

Purpose of the Study:

  • To review and classify the diverse synthetic methodologies for thiochromene compounds.
  • To discuss reaction mechanisms, conditions, and key examples for each synthetic approach.
  • To identify gaps and opportunities in thiochromene synthesis for novel drug discovery.

Main Methods:

  • Classification of synthetic routes including Michael addition, cycloaddition, ring-opening, coupling, cyclization, and Diels-Alder reactions.
  • Discussion of reaction mechanisms, conditions, and specific examples for each method.
  • Highlighting the role of chiral catalysts, substrates, and reaction parameters in achieving selectivity and yield.

Main Results:

  • Michael addition, cycloaddition, ring-opening, coupling, cyclization, and Diels-Alder reactions are effective for thiochromene synthesis.
  • Chiral catalysts and specific substrates enable enantioselectivity and regioselectivity.
  • Palladium catalysts are crucial for coupling reactions, while controlled conditions are vital for cyclization and Diels-Alder reactions.

Conclusions:

  • Thiochromene synthesis is achievable through various well-established organic reactions.
  • Optimized synthetic strategies can lead to diverse and novel thiochromene derivatives for drug discovery.
  • Further research into synthetic pathways can unlock new thiochromene-containing lead molecules.