191348-14-8Relevant articles and documents
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.
Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes
Peng, Xiaoshi,Zhu, Lifeng,Hou, Yuqian,Pang, Yadong,Li, Yangming,Fu, Jiayue,Yang, Lu,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
supporting information, p. 3402 - 3405 (2017/07/15)
The cyclization order of the difunctional 1,2-diphenylethynes was precisely tuned under the catalysis of gold by changing the nitrogen substitution of the substrates, leading to the facile preparation of benzo[a]carbazole and indeno[1,2-c]quinoline derivatives. The mechanisms of these domino cyclizations were probed by control experiments, and an insight into the selectivity of the cyclization was gained by density functional theory (DFT) calculations. This research represents a unified and common method to access benzo[a]carbazoles and indeno[1,2-c]quinolines.
Synthesis of carbazoles based on gold-copper tandem catalysis
Choi, Subin,Srinivasulu, Vunnam,Ha, Sujin,Park, Cheol-Min
supporting information, p. 3481 - 3484 (2017/03/29)
An efficient synthetic method for carbazoles has been developed employing diazo anilinoalkynes as substrates. Sequential activation of the orthogonal functional groups embedded in diazo anilinoalkyne substrates by tandem gold-copper catalysis leads to the formation of highly substituted carbazoles. Substrate scope reveals a broad tolerability toward the substitution on aryl groups.
A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
supporting information, p. 2127 - 2133 (2016/02/18)
The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1,3-enynes bearing a trifluoromethyl group on their terminal sp2 carbon. The subsequent cyclization of these 1,3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3,3,3-trifluoroprop-1-enyl group at their 2-position.
One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay
supporting information, p. 10987 - 10999 (2016/11/28)
A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.
Design, Synthesis and in vitro Evaluation of Indolotacrine Analogues as Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease
Benek, Ondrej,Soukup, Ondrej,Pasdiorova, Marketa,Hroch, Lukas,Sepsova, Vendula,Jost, Petr,Hrabinova, Martina,Jun, Daniel,Kuca, Kamil,Zala, Dominykas,Ramsay, Rona R.,Marco-Contelles, José,Musilek, Kamil
supporting information, p. 1264 - 1269 (2016/08/06)
Novel indolotacrine analogues were designed, synthesized, and evaluated as potential drugs for the treatment of Alzheimer's disease. By using a multitarget-directed ligand approach, compounds were designed to act simultaneously as cholinesterase (ChE) and
Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions
Alikarami, Mohammad,Nazarzadeh, Somayeh,Soleiman-Beigi, Mohammad
, p. 157 - 162 (2015/01/30)
1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.
Substituent effects on stoichiometric and catalytic cleavage of carbon-nitrogen bonds in aniline derivatives by ruthenium-phosphine complexes
Koreeda, Tetsuro,Kochi, Takuya,Kakiuchi, Fumitoshi
, p. 682 - 690 (2013/03/14)
The reactivity of various o-acylaniline derivatives with ruthenium complexes was examined. The reaction of o-acylanilines with RuH 2(CO)(PPh3)3 (1) or an activated ruthenium species formulated as "Ru(CO)(PPh3)s
Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid
Miyamoto, Hiroshi,Hirano, Tomohiro,Okawa, Yoichiro,Nakazaki, Atsuo,Kobayashi, Susumu
supporting information, p. 9481 - 9493 (2013/10/08)
An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.
Consecutive gold(I)-catalyzed cyclization reactions of o -(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas: A one-pot synthesis of pyrimido[1,6- a ]indol-1(2 H)-ones and related systems
Sharp, Phillip P.,Banwell, Martin G.,Renner, Jens,Lohmann, Klaas,Willis, Anthony C.
supporting information, p. 2616 - 2619 (2013/07/11)
Treatment of readily available o-(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas such as 1 with the Au(I)-catalyst 11 affords, via a twofold cyclization process, the isomeric pyrimido[1,6-a]indol-1(2H)-one 3 in good yield.
