cas 1859-39-8, 1-hydroxy-2-phenyl-1H-indole

Articles about 1859-39-8Total 5 be found

A General Synthesis of N-Hydroxyindoles
A general method for the formation of N-hydroxyindoles is demonstrated through a lead-promoted intramolecular reductive cyclization of o-nitrobenzyl ketones and aldehydes under transfer hydrogenation conditions. The N-hydroxyindoles are isolated in high purity and excellent yield (> 90%) in an operationally simple procedure. This new method is exemplified by a two-step synthesis of the naturally occurring 1-methoxyindole-3-carboxaldehyde, which is pivotal in many alkaloid total syntheses.
Wong, Audrey,Kuethe, Jeffrey T.,Davies, Ian W.
p. 9865 - 9866
(2003)
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Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles
tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.
Driver, Tom G.,Sung, Siyoung,Wink, Donald J.,Zadrozny, Joseph M.,Zhao, Yingwei,Zhu, Haoran
p. 19207 - 19213
(2021/08/09)

Synthesis of N-Hydroxyindole Derivatives via Pd-Catalyzed Electrophilic Cyclization
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Oh, Soo Min,Shin, Seunghoon
p. 925 - 928
(2021/05/17)

Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant
Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.
Shevlin, Michael,Guan, Xinyu,Driver, Tom G.
p. 5518 - 5522
(2017/08/17)

Reductive cyclizations of nitroarenes to hydroxamic acids by visible light photoredox catalysis
We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated. Georg Thieme Verlag Stuttgart New York.
Cismesia, Megan A.,Ischay, Michael A.,Yoon, Tehshik P.
p. 2699 - 2705
(2013/10/21)