275361-75-6Relevant academic research and scientific papers
Photoredox Catalysis toward 2-Sulfenylindole Synthesis through a Radical Cascade Process
Betim, Hugo L. I.,Campos Delgado, Jose Antonio,Corrêa, Arlene G.,Kisukuri, Camila M.,Paix?o, Márcio W.,Santos, Marilia S.
, p. 4266 - 4271 (2020/06/27)
A radical cascade process initiated through visible-light induced thiyl radical coupling with ortho-substituted arylisocianides followed by an intramolecular cyclization and subsequent aromatization to access 2-sulfenylindoles is described. The key thiyl radicals are promptly generated via a hydrogen atom transfer event. The redox-neutral protocol features broad substrate scope, excellent functional group tolerance, and mild reaction conditions. Furthermore, the implementation of a continuous flow variant allows smooth scalability with a short residence time through process intensification.
Copper-Catalyzed Dihydroquinolinone Synthesis from Isocyanides and O-Benzoyl Hydroxylamines
Yang, Zhen,Jiang, Kun,Chen, Ying-Chun,Wei, Ye
, p. 3725 - 3734 (2019/03/20)
A copper-catalyzed protocol has been realized for the rapid assembly of dihydroquinolinones from readily accessible isocyanides and O-benzoyl hydroxylamines. The reactions (10 mol % of CuOAc, 10 mol % of dppe, 3 equiv of PhONa, 30 °C) deliver various stru
Photoinduced intramolecular cyclization of o -ethenylaryl isocyanides with organic disulfides mediated by diphenyl ditelluride
Mitamura, Takenori,Iwata, Kimiyo,Ogawa, Akiya
, p. 3880 - 3887 (2011/07/09)
Photoinduced reaction of o-ethenylaryl isocyanides with organic disulfides in the presence of diphenyl ditellurides affords the corresponding bisthiolated indole derivatives via a radical cyclization process. The cyclization can proceed at room temperature upon visible-light irradiation and exhibits good tolerance to functional groups. Several organic disulfides also can be employed for this cyclization, and the corresponding bisthiolated indole derivatives are obtained selectively. In addition, the photoinduced reaction of o-ethenylaryl isocyanides with bis(2-aminophenyl) disulfide affords tetracyclic compounds in one portion.
Synthesis of 2-(2-Dialkylamino-4 H -3,1-benzothiazin-4-yl)acetic acid derivatives and 2-(2-Thioxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetic Acid derivatives
Fukamachi, Shuhei,Konishi, Hisatoshi,Kobayashi, Kazuhiro
experimental part, p. 1593 - 1598 (2010/06/21)
An efficient method for the preparation of 2-(4H-3,1-benzothiazin-4-yl) acetic acid derivatives and 2-(2-thioxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetic acid derivatives has been developed. The reaction of 3-(2-isothiocyanatophenyl) propenoic acid derivatives with secondary amines in methanol at room temperature gave the corresponding thiourea intermediates, which on heating at reflux temperature cyclized by an attack of the sulfur atom on the propenoic moiety in a 1,4-addition manner, to give 2-(2-dialkylamino-4H-3,1-benzothiazin-4-yl)acetic acid derivatives in one pot. A similar sequence using primary amines in place of secondary amines afforded 2-[3-alkyl(or aryl)-2-thioxo-1,2,3,4- tetrahydroquinazolin-4-yl]acetic acid derivatives. Georg Thieme Verlag Stuttgart.
