Computed Properties of C8H6FNIn 2019 ,《Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot》 was published in Journal of Organic Chemistry. The article was written by Equbal, Danish; Singh, Richa; Saima; Lavekar, Aditya G.; Sinha, Arun K.. The article contains the following contents:
Bifunctionalized indoles are an important class of biol. active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge. To expand this field, we herein disclose a step-economical and temperature tunable strategy wherein the synergistic effect between [hmim]Br-ArSO2Cl leads exclusively to the formation of 3-arylthio indole via sulfenylation of indole at room temperature, while heating the reaction mixture at 50 °C provided an unexpected 2-halo-3-arylthio indole with construction of C-S and C-S/C-X (X = Cl and Br) bonds without addition of any external halogenating agent via cascade sulfenylation-halogenation reactions under metal-oxidant-base-free conditions. Further, insight into the reaction mechanism provides an unprecedented observation wherein the synergistic interaction between [hmim]Br-ArSO2X in the presence of a catalytic amount of water generates arylsulfonic anhydride (ArSO2)2O in situ as a new sulfur source along with the formation of [hmim]PTS as probed by NMR, ESI-MS, DART-MS, and HPLC studies. Notably, the mixture of bifunctionalized 2-halo(Br/Cl)-3-arylthio indole was smoothly diversified with privileged heterocycle triazole to provide 2-(1H-triazole-1-yl)-3-arylthio indole, which is an analog of the potent indole-based anticancer agent. In the experiment, the researchers used many compounds, for example, 5-Fluoro-1H-indole(cas: 399-52-0Computed Properties of C8H6FN)
5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Computed Properties of C8H6FN
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles