948-65-2Relevant articles and documents
Gold-Catalyzed Synthesis of Dibenzo[1,5]diazocines from β-(2-Aminophenyl)-α,β-ynones
Rode, Navnath D.,Arcadi, Antonio,Chiarini, Marco,Marinelli, Fabio,Portalone, Gustavo
, p. 3371 - 3377 (2017)
β-(2-Aminophenyl)-α,β-ynones afforded exclusively challenging dibenzo[1,5]diazocines by means of (JonPhosAuNCMe)SbF6 catalysis. In contrast with the known gold-catalyzed reaction path of 2-alkynylanilines that leads to indoles, ynones underwent an auto intermolecular hydroamination. This process resulted finally in the formation of an eight-membered ring, likely through a selective 8-exo-dig intramolecular hydroamination that prevailed over the possible cyclocondensation reaction (that would result in the formation of 4-aminoquinoline derivatives). The easy availability of β-(2-aminophenyl)-α,β-ynones and the simple cyclization procedure make this approach suitable for the preparation of a wide range of useful dibenzodiazocines. The methodology can be extended to the use of β-(2-aminophenyl)-α,β-ynoates as substrates. (Figure presented.).
A Cascade Synthesis of Hetero-arylated Triarylmethanes Through a Double 5-endo-dig Cyclization Sequence
Paluru, Dilip K.,Mahesh, Sriram,Ahmad, Feroz,Vijaya Anand, Ramasamy
, p. 4688 - 4695 (2019)
A sequential two-step method for the synthesis of hetero-arylated triarylmethanes through a Ag-catalyzed sequential double cyclization–nucleophilic addition cascade is described. This methodology basically involves an initial 5-endo-dig cyclization of o-alkynyl anilines to provide 2-substituted indole derivatives, which then react with 2-(2-enynyl)-pyridines to afford indolizine-containing unsymmetrical triarylmethanes through another 5-endo-dig cyclization.
Ga(OTf)3-Catalyzed Temperature-Controlled Regioselective Friedel-Crafts Alkylation of Trifluoromethylated 3-Indolylmethanols with 2-Substituted Indoles: Divergent Synthesis of Trifluoromethylated Unsymmetrical 3,3′-and 3,6′-Bis(indolyl)methanes
Ling, Yuan,An, Di,Zhou, Yuanyuan,Rao, Weidong
, p. 3396 - 3401 (2019)
An unprecedented Ga(OTf)3-catalyzed, temperature-controlled regiodivergent alkylation of 2-substituted indoles with trifluoromethylated 3-indolylmethanols is described that provides structurally diverse unsymmetrical 3,3′- and 3,6′-bis(indolyl)methanes with a CF3-containing quaternary carbon center in good to excellent yields under mild conditions. In addition, this present protocol could be successfully extended to the synthesis of difluoromethylated 3,3′- and 3,6′-bis(indolyl)methanes with excellent efficiency.
SYNTHESIS OF 2-SUBSTITUTED INDOLES
Zav'yalov, S. I.,Zavozin, A. G.,Dorofeeva, O. V.,Rumyantseva, E. E.
, p. 441 - 443 (1991)
2-Substituted indoles are obtained upon the cyclocondensation of (2-R-2-oxoethyl)trimethylammonium bromides.
Three-component Au—Chitosan—SiO2 systems as heterogeneous catalysts for intramolecular cyclization of 2-(2-phenylethynyl)aniline
Finashina,Tkachenko,Startseva, A. Yu.,Krasovsky,Kustov,Beletskaya
, p. 2816 - 2820 (2015)
A series of three-component heterogeneous catalysts Au—Ch—SiO2 with Ch for chitosan was prepared. The size of gold nanoparticles immobilized on the chitosan matrix depends on the method of sample preparation. The particles with the size 2. The catalysts were tested in the intramolecular cyclization reaction of 2-(2-phenylethynyl)aniline to for 2-phenylindole. The maximum conversion of 2-(2-phenylethynyl)aniline (25% within 35 h) was obtained on the Au(0.4%)—Ch(2.9%)/SiO2 catalyst.
Domino cyclization-alkylation protocol for the synthesis of 2,3-functionalized indoles from o-alkynylanilines and allylic alcohols
Xu, Chang,Murugan, Vinod K.,Pullarkat, Sumod A.
, p. 3875 - 3881 (2012)
A practical and efficient protocol for the one-pot synthesis of 2,3-substituted indoles was developed via a palladacycle catalyzed domino cyclization-alkylation reaction involving 2-alkynylanilines and allylic alcohols under mild conditions without any additives.
Recent developments in hybrid iron oxide–noble metal nanocatalysts for organic reactions
Woo, Hyunje,Park, Kang Hyun
, p. 209 - 226 (2016)
A review of recent developments in the synthesis of hybrid iron oxide–noble metal nanocomposites and their application to various organic reactions is presented herein. Focus is placed on various strategies for achieving (1) Au nanoparticles (NPs) on Fe3O4@polymer catalysts, (2) optimized dispersion and stability of Fe3O4/Pd catalysts, (3) Au NPs supported on Fe2O3–graphene oxide hybrid nanosheets and (4) rose-like Pd–Fe3O4 hybrid nanocomposite-supported Au nanocatalysts. Further application of such hybrid nanocomposites as catalysts for various organic reactions is discussed in brief.
Chiral-Phosphoric-Acid-Catalyzed C6-Selective Pictet-Spengler Reactions for Construction of Polycyclic Indoles Containing Spiro Quaternary Stereocenters
Huang, Wen-Jun,Wang, Han,Wang, Xin-Wei,Wu, Bo,Zhou, Yong-Gui
supporting information, p. 1727 - 1731 (2022/03/14)
Compared with the well-established asymmetric Pictet-Spengler reactions on the pyrrole ring of indoles, the catalytic asymmetric Pictet-Spengler reaction on the benzene ring of indoles has been rarely studied. Herein the C6-selective Pictet-Spengler react
Modular counter-Fischer?indole synthesis through radical-enolate coupling
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
supporting information, p. 1096 - 1102 (2021/01/26)
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.