Late-stage sulfonic acid/sulfonate formation from sulfonamides via sulfonyl pyrroles

Ozaki, Tomoya; Yorimitsu, Hideki; Perry, Gregory J. P.

doi:10.1016/j.tet.2022.132830

Cited by 9 publications

(6 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…25 During the treatment of 2 with KOH, a slight amount of precipitate is formed, similar to attempts in literature. 26 1 H-NMR analysis of this residue reveals the successful post-polymerization modification (see ESI S8 †). After dialysis, excess salt is removed yielding <1% of 2a.…”

Section: Polymer Chemistry Papermentioning

confidence: 98%

Synthesis of a sulfonamide functionalized poly(styrene oxide) and illustration of a potential post-polymerization strategy

Wittig,

Pfändner,

Rieger

2024

Polym. Chem.

View full text Add to dashboard Cite

show abstract

Section: Polymer Chemistry Papermentioning

confidence: 98%

Synthesis of a sulfonamide functionalized poly(styrene oxide) and illustration of a potential post-polymerization strategy

Wittig,

Pfändner,

Rieger

2024

Polym. Chem.

View full text Add to dashboard Cite

show abstract

“…In another report, Ozaki et al [ 87 ] used the Clauson–Kaas approach to synthesize sulfonic acids/sulfonates from various primary sulfonamides via sulfonylpyrroles. First, various sulfonylpyrroles 69 were prepared from primary sulfonamides 68 by reaction with 2,5-DMTHF ( 2 ) using two methods as shown in Scheme 33 .…”

Section: Reviewmentioning

confidence: 99%

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

Singh¹,

Kumar²

2023

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Pyrrole is an important aromatic heterocyclic scaffold found in many natural products and predominantly used in pharmaceuticals. Continuous efforts are being made to design and synthesize various pyrrole derivatives using different synthetic procedures. Among them, the Clauson–Kaas reaction is a very old and well-known method for synthesizing a large number of N-substituted pyrroles. In recent years, due to global warming and environmental concern, research laboratories and pharmaceutical industries around the world are searching for more environmentally friendly reaction conditions for synthesizing compounds. As a result, this review describes the use of various eco-friendly greener protocols to synthesize N-substituted pyrroles. This synthesis involves the reaction of various aliphatic/aromatic primary amines, and sulfonyl primary amines with 2,5-dimethoxytetrahydrofuran in the presence of numerous acid catalysts and transition metal catalysts. The goal of this review is to summarize the synthesis of various N-substituted pyrrole derivatives using a modified Clauson–Kaas reaction under diverse conventional and greener reaction conditions.

show abstract

“…As part of the study of methods for the synthesis of antiviral drugs based on sulfonamides, it is worth noting the unique reaction presented in Scheme 7. This reaction is a simple and effective method for obtaining substituted pyrrole 34 from primary sulfonamide 33 [53]: Scheme 6. Reaction of 6-chloro-4,5-dihydro-7H-purine with sulfamide derivatives.…”

Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 99%

“…The formation of sulfonylpyrrole 34 proceeded via the reaction of sulfonamide and 2,5-dimethoxytetrahydrofuran (diMeOTHF) 32 in the presence of a catalytic amount of p-TsOH (similar to the reaction of sulfonylpyridinium salts [54]). The reaction was also carried out with microwave activation without solvent and additives at 150 • C [53]. The method may be of interest for the synthesis of antiviral drugs, since antiviral biological activity is known for sulfonamide-containing pyrroles [55].…”

Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 99%

Sulfonamides with Heterocyclic Periphery as Antiviral Agents

Moskalik

2022

Molecules

View full text Add to dashboard Cite

Sulfonamides are the basic motifs for a whole generation of drugs from a large group of antibiotics. Currently, research in the field of the new sulfonamide synthesis has received a “second wind”, due to the increase in the synthetic capabilities of organic chemistry and the study of their medical and biological properties of a wide spectrum of biological activity. New reagents and new reactions make it possible to significantly increase the number of compounds with a sulfonamide fragment in combination with other important pharmacophore groups, such as, for example, a wide class of N-containing heterocycles. The result of these synthetic possibilities is the extension of the activity spectrum—along with antibacterial activity, many of them exhibit other types of biological activity. Antiviral activity is also observed in a wide range of sulfonamide derivatives. This review provides examples of the synthesis of sulfonamide compounds with antiviral properties that can be used to develop drugs against coxsackievirus B, enteroviruses, encephalomyocarditis viruses, adenoviruses, human parainfluenza viruses, Ebola virus, Marburg virus, SARS-CoV-2, HIV and others. Since over the past three years, viral infections have become a special problem for public health throughout the world, the development of new broad-spectrum antiviral drugs is an extremely important task for synthetic organic and medicinal chemistry. Sulfonamides can be both sources of nitrogen for building a nitrogen-containing heterocyclic core and the side chain substituents of a biologically active substance. The formation of the sulfonamide group is often achieved by the reaction of the N-nucleophilic center in the substrate molecule with the corresponding sulfonylchloride. Another approach involves the use of sulfonamides as the reagents for building a nitrogen-containing framework.

show abstract

Late-stage sulfonic acid/sulfonate formation from sulfonamides via sulfonyl pyrroles

Cited by 9 publications

References 43 publications

Synthesis of a sulfonamide functionalized poly(styrene oxide) and illustration of a potential post-polymerization strategy

Synthesis of a sulfonamide functionalized poly(styrene oxide) and illustration of a potential post-polymerization strategy

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

Sulfonamides with Heterocyclic Periphery as Antiviral Agents

Contact Info

Product

Resources

About