A Novel Synthesis of Sulfone Systems as Antimicrobial Agents

Abstract

The applicability and synthetic potency of novel reagent, 2-aryl-1,1-dicyano-3-(phenylsulfo-nyl)propenes 3 to develop an expeditious convenient synthetic route of unique polyfunctionally substituted carbocyclic and heterocyclic sulfone systems is reported. Chemical and spec­troscopic evidence for the structures of the newly synthesized compounds are described. Some of the obtained compounds were tested for their antimicrobial activity

Copper‐Catalyzed Direct C−H Bond Oxidative Sulfonylation of β‐Alkyl Cyanoalkenes with Sodium Sulfinates

“…However, the synthesis of these compounds has not been extensively documented in the past. In 1999, Erian and his co‐workers reported a two‐step strategy involving the use of a Br‐substituted intermediate followed by nucleophilic substitution of sodium arylsulfinates [9] . Another strategy involved the condensation of ethynyl sulfones and sodium malonitrile with NaH in anhydrous THF [10] .…”

“…In 1999, Erian and his co-workers reported a two-step strategy involving the use of a Br-substituted intermediate followed by nucleophilic substitution of sodium arylsulfinates. [9] Another strategy involved the condensation of ethynyl sulfones and sodium malonitrile with NaH in anhydrous THF. [10] These strategies were subject to the harsh reaction conditions and starting materials that were not readily available.…”

Stereospecific Syntheses of Enaminonitriles and β-Enaminoesters via Domino Ring-Opening Cyclization (DROC) of Activated Cyclopropanes with Pronucleophilic Malononitriles

“…Five-membered carbocyclic enaminonitriles and β-enaminoesters, as shown in Figure , are ubiquitous structural motifs in natural products and other synthetic compounds with a wide spectrum of biological activities. I having a five-membered enaminonitrile framework exhibits antiviral activity against HSV-1 and HIV-1, and II , also possessing the same structural core, exhibits a limited antimicrobial activity . However, five-membered β-enaminoester motif-bearing compounds III and IV exhibit lifespan-altering properties in eukaryotic organisms…”

“…I having a five-membered enaminonitrile framework exhibits antiviral activity against HSV-1 and HIV-1, 1 and II, also possessing the same structural core, exhibits a limited antimicrobial activity. 2 However, five-membered β-enaminoester motif-bearing compounds III and IV exhibit lifespan-altering properties in eukaryotic organisms. 3 Owing to the presence of the aforementioned enaminonitrile scaffold in beneficial bioactive compounds, a number of reports exists in the literature for the synthesis of five-membered carbocyclic enaminonitriles.…”

Heterocyclic sulfones. Part IV. A novel synthesis of pyrrole and fused heterocyclic sulfones

“…In view of the diverse biological and physiological activities of sulfones, 1-7 and in connection with our previous efforts directed towards the simple synthesis of heterocyclic ring systems, 8- 13 we designed a specific simple programme aimed at the development of convenient synthetic approaches to heterocyclic sulfone systems of expected potential bioresponses, utilizing the novel reagents 3 as unique key precursors. The newly synthesised sulfone derivatives appear to be promising for further chemical transformations as well as biological activity evaluations.…”