81787-92-0Relevant academic research and scientific papers
Copper(II)-Catalyzed Direct C-H (Hetero)arylation at the C3 Position of Indoles Assisted by a Removable N, N-Bidentate Auxiliary Moiety
Xu, Hai-Feng,Pan, You-Lu,Li, Gang-Jian,Hu, Xu-Yang,Chen, Jian-Zhong
, p. 1789 - 1801 (2021/02/03)
The regioselective arylation of inert C3-H bonds in indoles reacting with arylboronates via effective copper-mediated catalysis with the aid of a facile and removable 2-pyridinylisopropyl (PIP) group without ligand participation is reported. This newly established method features high compatibility with diverse functional groups between coupling partners, including both indole substrates and arylboron reagents, consequentially leading to operational simplicity and providing access to generate the desired arylated products in good to excellent yields of up to 97%. Synthetically, the PIP-derived amide moiety could subsequently be readily removed under mild reaction conditions to produce useful indole carboxylic acids for further transformation.
Calcium-Catalyzed Formal [5 + 2] Cycloadditions of Alkylidene β-Ketoesters with Olefins: Chemodivergent Synthesis of Highly Functionalized Cyclohepta[ b]indole Derivatives
Parker, Ariel N.,Martin, M. Cynthia,Shenje, Raynold,France, Stefan
supporting information, p. 7268 - 7273 (2019/10/08)
The calcium-catalyzed, formal [5 + 2] cycloaddition of indolyl alkylidene β-ketoesters with mono- A nd disubstituted aryl olefins to form cyclohepta[b]indole derivatives has been established. Unanticipated chemodivergence with phenyl vinyl sulfide/ether revealed a double [5 + 2] cycloaddition cascade providing ethano-bridged cyclohepta[b]indoles. Overall, the method's highlights include: (1) use of a green, calcium-based catalyst (2.5 mol % loading); (2) reaction times under 1 h; (3) mild reaction conditions; (4) substrate-derived chemodivergence; (5) functional group tolerance; and (6) examples of derivatization.
Synthesis of carbazoles by gold(I)-catalyzed carbocyclization of 2-(enynyl)indoles
Praveen, Chandrasekaran,Perumal, Paramasivan Thirumalai
scheme or table, p. 521 - 524 (2011/04/17)
A new synthetic protocol for carbazoles through gold(I)-catalyzed intramolecular hydroarylation of (Z)-2-(enynyl)indoles was achieved in good yields. The requisite (Z)-2-(enynyl)indoles were synthesized stereoselectively by trimethylgallium-promoted, Z-selective Wittig olefination of N-alkylindole-2-carboxaldehydes with propargyl ylides. Substrates possessing both alkyl as well as aromatic groups are well tolerated under these reaction conditions. Georg Thieme Verlag Stuttgart.
CH activation and CH2 double activation of indolines by radical translocation: Understanding the chemistry of the indolinyl radical
Harrowven, David C.,Stenning, Kerri J.,Whiting, Sally,Thompson, Toby,Walton, Robert
, p. 4882 - 4885 (2011/08/05)
CH activation and CH2 double activation of indolines at C2 may be achieved efficiently through radical translocation. The fate of the C2 indolinyl radical is dictated by the substitution at C3. Fragmentation, cyclisation and tandem cyclisation reactions leading to indole, azaheterocycle and azapropellane formation, respectively, are reported. The Royal Society of Chemistry 2011.
Tandem palladium-catalyzed N,C-coupling/carbonylation sequence for the synthesis of 2-carboxyindoles
Vieira, Tiago O.,Meaney, Laura A.,Shi, Yong-Ling,Alper, Howard
supporting information; experimental part, p. 4899 - 4901 (2009/05/31)
(Chemical Equation Presented) Tandem palladium-catalyzed N,C-coupling/carbonylation, under 10 aim of carbon monoxide and at 110 °C, is a novel and efficient method for the preparation of 2-carboxyindoles. The catalyst system tolerates a variety of functional groups, and the noted indoles were obtained in good isolated yields.
Enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indoles
Li, Chang-Feng,Liu, Hiu,Liao, Jie,Cao, Yi-Ju,Liu, Xiao-Peng,Xiao, Wen-Jing
, p. 1847 - 1850 (2008/02/02)
An enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indolyl α,β-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs and THBCs in a straightforward and a
SmI2-promoted radical addition reactions with N-(2-indolylacyl)oxazolidinones: Synthesis of bisindole compounds
Lindsay, Karl B.,Ferrando, Francese,Christensen, Kasper L.,Overgaard, Jacob,Roca, Tomas,Bennasar, M.-Lluisa,Skrydstrup, Troels
, p. 4181 - 4188 (2008/02/04)
(Chemical Equation Presented) The treatment of N-acyl oxazolidinones of N-benzyl 2-indolecarboxylic acids varying in the substitution pattern of the indole ring with samarium diiodi de at -78°C led to the formation of two indole dimer products. The major product isolated in yields from 55 to 59% represents an unsymmetrical dimer arising from 1,4-addition to the 2-indolecarboxylic acid derivative of a possible ketyl-type radical anion intermediate originating from the reduction of the exocyclic carbonyl group of the N-acyl oxazolidinone. The minor dimer, represented by a symmetrical diketone, was produced in yields ranging from 11 to 23%. Even in the presence of an α,β-unsaturated amide, dimerization was the preferred pathway rather than the formation of a γ-keto amide. Upon treatment with acid, the unsymmetrical indole dimer cyclized to form a diindolequinone. Finally, the N-acyl oxazolidinones of pyrrole-2-carboxylic acid and 3 indolecarboxylic acid preferred in both cases to undergo C-C bond formation with an acrylamide in the presence of SmI2 rather than dimerization.
Intramolecular reactions of 2-indolylacyl radicals: Cyclisation upon aromatic rings
Bennasar, M.-Llu?sa,Roca, Tomàs,Ferrando, Francesc
, p. 5605 - 5609 (2007/10/03)
The generation of 2-indolylacyl radicals from the corresponding selenoesters under reductive (tributyltin hydride-AIBN) and nonreductive (hexabutylditin, 300W) conditions and their behaviour in cyclisation reactions upon benzene rings attached either to t
Syntheses and biological evaluation of indole-2 and 3-carboxamides: New selective cyclooxygenase-2 inhibitors
Oelgen, Suereyya,Guener,Fabregat,Crespo,Nebioglu
, p. 238 - 242 (2007/10/03)
A series of indol-2 and 3-carboxamides were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1). Substitution on indol nitrogen with benzyl and p-fluorobenzyl group of indole-2 carboxamides 8, 10, 11 provides fairly active COX-2 enzyme inhibitors.
Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors
Olgen, Sureyya,Akaho, Eiichi,Nebioglu, Dogu
, p. 747 - 770 (2007/10/03)
A series of N-substituted indole-2-carboxylic acid esters have been prepared by replacing the benzoyl group of indomethacin with a benzyl and a phenyl group. The carbocyclic acid side chain was extended via creating an ester structure by using several dialkylaminoalkyl groups. The receptor docking studies were performed to investigate the docking mode of each compound by using dock 4.0. All the compounds were shown to be docked at the site where intact flurbiprofen was embedded for COX-1 and s-58 (1-phenylsulphonamide-3-trifluoromethyl-5-para-bromophenylpyrazole) for COX-2. It was predicted that N-phenyl-indole-2-carboxylic acid piperazine ester 22 can be a fairly strong COX-2 selective compound which was compared to the others. Other predicted COX-2 selective compounds included are N-H indole-2-carboxylic acid diethyl 30 and piperazine 34 esters. In view of these findings, compounds 22, 30 and 34 were chosen for the in vitro biological assays.
