139461-66-8Relevant academic research and scientific papers
Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides
Zhou, Shiping,Xiao, Genhua,Liang, Yun
, p. 338 - 341 (2017)
A novel and efficient method for synthesis of 2-sulfenylindole via copper-catalyzed coupling reaction of indoline-2-thiones with aryl iodides has been developed. A series of N-substituted and N-free 2-sulfenylindole were obtained in high yields. Furthermo
Design synthesis and evaluation of novel aldose reductase inhibitors: The case of indolyl–sulfonyl–phenols
Koutsopoulos, Konstantinos,Lavrentaki, Vasiliki,Antoniou, Ioakeim,Kousaxidis, Antonios,Lefkopoulou, Matina,Tsantili-Kakoulidou, Anna,Kovacikova, Lucia,Stefek, Milan,Nicolaou, Ioannis
, (2020/06/17)
Therapeutic interventions with aldose reductase inhibitors appear to be a promising approach to major pathological conditions (i.e. neuropathy/angiopathy related to chronic hyperglycemia, chronic inflammation and cancer). Until now, the most potent aldose
TFA-promoted direct C-H sulfenylation at the C2 position of non-protected indoles
Hostier, Thomas,Ferey, Vincent,Ricci, Gino,Pardo, Domingo Gomez,Cossy, Janine
, p. 13898 - 13901 (2015/09/07)
A simple, efficient and practical metal-free C-H sulfenylation process at the C2 position of non-protected indoles has been developed. 2-Thioindoles were obtained in moderate to high yields using stable and readily available N-(thio)succinimides at room temperature in the presence of TFA.
Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides
Hamel, Pierre,Zajac, Nicolas,Atkinson, Joseph G.,Girard, Yves
, p. 6372 - 6377 (2007/10/02)
Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction.We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring.In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched.Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides.This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.
Acid-catalyzed Isomerization of 3-Indolyl Sulfides to 2-Indolyl Sulfides: First Synthesis of 3-Unsubstituted 2-(Arylthio)indoles. Evidence for a Complex intermolecular Process
Hamel, Pierre,Girard, Yves,Atkinson, Joseph G.
, p. 2694 - 2699 (2007/10/02)
The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds.When catalyzed by trifluoracetic acid, the isomerisation proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction if these species to yield the rearranged isomer 4.A mechanism is proposed involving a role for the acid tn the sulfenyl-transfer steps.This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.
