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Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
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.
5.1K
Drug Metabolism: Phase II Reactions01:14

Drug Metabolism: Phase II Reactions

4.1K
Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
4.1K
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

393
Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
393
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
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...
2.0K
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

3.7K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
3.7K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K

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

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Modular Two-Step Route to Sulfondiimidamides.

Ze-Xin Zhang1, Charles Bell1, Mingyan Ding1

  • 1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.

Journal of the American Chemical Society
|June 22, 2022
PubMed
Summary
This summary is machine-generated.

A new two-step synthesis enables the creation of sulfondiimidamides, a class of molecules previously difficult to access. This breakthrough offers a simpler and more efficient route for discovering new bioactive compounds containing these important sulfur functional groups.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Sulfur functional groups are vital in bioactive molecules, with sulfonamides being common.
  • Aza-derivatives like sulfoximines and sulfonimidamides are gaining interest.
  • Sulfondiimidamides, double aza-variants, are largely unexplored due to synthetic challenges.

Purpose of the Study:

  • To develop an efficient and accessible synthetic route for sulfondiimidamides.
  • To overcome limitations of existing multi-step and capricious synthetic methods.
  • To facilitate the application of sulfondiimidamides in discovery chemistry.

Main Methods:

  • A two-step synthesis was developed for sulfondiimidamides.
  • The key step involved a hypervalent iodine-mediated amination.
  • Starting materials included organometallic reagents, unsymmetrical sulfurdiimides, and amines.

Main Results:

  • >40 examples of sulfondiimidamides were synthesized.
  • The method produced derivatives of three sulfonamide-based drugs.
  • The synthesis demonstrated operational simplicity, broad scope, and conciseness.

Conclusions:

  • The developed method provides a practical and efficient route to sulfondiimidamides.
  • This approach significantly enhances the accessibility of sulfondiimidamides for drug discovery.
  • The operational simplicity makes it attractive for broad application in discovery chemistry.