- 3-aryl-indolinones derivatives as antiplasmodial agents: synthesis, biological activity and computational analysis
-
Malaria is an infectious illness, affecting vulnerable populations in Third World countries. Inspired by natural products, indole alkaloids have been used as a nucleus to design new antimalarial drugs. So, eighteen oxindole derivatives, aza analogues were obtained with moderate to excellent yields. Also, the saturated derivatives of oxindole and aza derivatives via H2/Pd/C reduction were obtained in good yields, leading to racemic mixtures of each compound. Next, the inhibitory activity against P. falciparum of 18 compounds were tested, founding six compounds with IC50 20 μM. The most active of these compounds was 8c; however, their unsaturated derivative 7c was inactive. Then, a structure-activity relationship analysis was done, founding that focused LUMO lobe on the specific molecular zone is related to inhibitory activity against P. falciparum. Finally, we found a potential inhibition of lactate dehydrogenase by oxindole derivatives, using molecular docking virtual screening.
- Luczywo, Ayelen,González, Lucía G.,Aguiar, Anna C. C.,Oliveira de Souza, Juliana,Souza, Guilherme E.,Oliva, Glaucius,Aguilar, Luis F.,Casal, Juan J.,Guido, Rafael V. C.,Asís, Silvia E.,Mellado, Marco
-
supporting information
(2021/03/18)
-
- Electrochemical Umpolung C-H Functionalization of Oxindoles
-
Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.
- Maulide, Nuno,Pastor, Miryam,Vayer, Marie,Weinstabl, Harald
-
supporting information
(2022/01/12)
-
- Activity-directed expansion of a series of antibacterial agents
-
The feasibility of using activity-directed synthesis to drive antibacterial discovery was investigated. An array of 220 Pd-catalysed microscale reactions was executed, and the crude product mixtures were evaluated for activity against Staphylococcus aureus. Scale-up of the hit reactions, purification and evaluation, enabled expansion of a class of antibacterial quinazolinones. The novel antibacterials had MICs from 0.016 μg mL-1 (i.e. 38 nM) to 2-4 μg mL-1 against S. aureus ATCC29213. This journal is
- Chow, Shiao,Clarke, Justin E.,Leggott, Abbie,Nelson, Adam,O'Neill, Alex J.,Warriner, Stuart L.
-
p. 8047 - 8050
(2020/08/03)
-
- Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols
-
A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50–92 % yield, 79 % average yield).
- Dambatta, Mubarak B.,Polidano, Kurt,Northey, Alexander D.,Williams, Jonathan M. J.,Morrill, Louis C.
-
p. 2345 - 2349
(2019/05/16)
-
- Pd(0)-Catalyzed Chemoselective Deacylative Alkylations (DaA) of N-Acyl 2-Oxindoles: Total Syntheses of Pyrrolidino[2,3- b]indoline Alkaloids, (±)-Deoxyeseroline, and (±)-Esermethole
-
We report an efficient Pd(0)-catalyzed deacylative allylation of N-acyl 3-substituted 2-oxindoles via the coupling of in situ generated nucleophiles (3 and 4) with allyl electrophiles for the synthesis of a variety of 2-oxindoles with C3-quaternary centers. Gratifyingly, this alkylation process is found to be highly chemoselective in nature, where a C-C bond formation is completely predominant over a C-N bond formation. A variety of key intermediates were synthesized utilizing an aforementioned methodology.
- Kumar, Nivesh,Gavit, Vipin R.,Maity, Arindam,Bisai, Alakesh
-
p. 10709 - 10735
(2018/09/29)
-
- Chiral N,N′-Dioxide/Scandium(III)-Catalyzed Asymmetric Alkylation of N-Unprotected 3-Substituted Oxindoles
-
An efficient enantioselective alkylation of N-unprotected 3-substituted oxindoles was realized by using a chiral N,N′-dioxide/scandium(III) complex as the catalyst. A wide range of 3,3-dialkyl substituted oxindoles with quaternary stereocenters were obtained in high yields and ee values (up to 98% yield and 99% ee). (Figure presented.).
- He, Changqiang,Cao, Weidi,Zhang, Jianlin,Ge, Shulin,Feng, Xiaoming
-
supporting information
p. 4301 - 4305
(2018/10/02)
-
- Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols
-
Herein we report the manganese-catalyzed C-C bond-forming reactions via α-alkylation of ketones, amides, and esters, using primary alcohols. β-Alkylation of secondary alcohols by primary alcohols to obtain α-alkylated ketones is also reported. The reactions are catalyzed by a (iPr-PNP)Mn(H)(CO)2 pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H2 in the case of secondary alcohol alkylation) as the sole byproduct.
- Chakraborty, Subrata,Daw, Prosenjit,Ben David, Yehoshoa,Milstein, David
-
p. 10300 - 10305
(2018/10/20)
-
- Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast
-
3-Substituted oxindoles are very interesting molecules both for their potential biological activity and for their role as starting materials toward more complex oxindole-based structures. These molecules can be prepared by the reduction of a 3-ylidene oxi
- Rossetti, Arianna,Sacchetti, Alessandro,Bonfanti, Marta,Roda, Gabriella,Rainoldi, Giulia,Silvani, Alessandra
-
p. 4584 - 4590
(2017/07/11)
-
- Oxidative Fragmentations and Skeletal Rearrangements of Oxindole Derivatives
-
An oxidative sequence for the conversion of oxindoles to structurally distinct heterocyclic scaffolds and aniline derivatives is disclosed by the combination of a copper-catalyzed C-H peroxidation and subsequent base-mediated fragmentation reaction. In contrast to classic enzymatic (i.e., kynurenine pathway) and biomimetic methods (i.e., Witkop-Winterfeldt oxidation) for oxidative indole cleavage, this protocol allows for the incorporation of external nucleophiles. The new transformation displays broad functional group tolerance and is applicable to tryptophan derivatives, opening potential new avenues for postsynthetic modification of polypeptides, bioconjugation, and unnatural amino acid synthesis.
- Klare, Hendrik F. T.,Goldberg, Alexander F. G.,Duquette, Douglas C.,Stoltz, Brian M.
-
supporting information
p. 988 - 991
(2017/03/14)
-
- Ionic Liquid-Mediated Hydrofluorination of o-Azaxylylenes Derived from 3-Bromooxindoles
-
The hydrofluorination reaction of 3-bromooxindole using mild HF reagents in an ionic liquid is described. This transformation can operate at room temperature to give a series of 3-substituted 3-fluorooxindole derivatives including racemic BMS 204352 (MaxiPost). The mechanistic study about interactions between HF and 3-butyl-1-methylimidazolium tetrafluoroborate [bmim][BF4] is also discussed on the basis of energy calculations.
- Mizuta, Satoshi,Otaki, Hiroki,Kitagawa, Ayako,Kitamura, Kanami,Morii, Yuki,Ishihara, Jun,Nishi, Kodai,Hashimoto, Ryo,Usui, Toshiya,Chiba, Kenya
-
supporting information
p. 2572 - 2575
(2017/05/24)
-
- Transition-metal-free Chemoselective Oxidative C?C Coupling of the sp3 C?H Bond of Oxindoles with Arenes and Addition to Alkene: Synthesis of 3-Aryl Oxindoles, and Benzofuro- and Indoloindoles
-
A transition-metal (TM)-free and halogen-free NaOtBu-mediated oxidative cross-coupling between the sp3 C?H bond of oxindoles and sp2 C?H bond of nitroarenes has been developed to access 3-aryl substituted and 3,3-aryldisubstituted oxindoles in DMSO at room temperature in a short time. Interestingly, the sp3 C?H bond of oxindoles could also react with styrene under TM-free conditions for the practical synthesis of quaternary 3,3-disubstituted oxindoles. The synthesized 3-oxindoles have also been further transformed into advanced heterocycles, that is, benzofuroindoles, indoloindoles, and substituted indoles. Mechanistic experiments of the reaction suggests the formation of an anion intermediate from the sp3 C?H bond of oxindole by tert-butoxide base in DMSO. The addition of nitrobenzene to the in-situ generated carbanion leads to the 3-(nitrophenyl)oxindolyl carbanion in DMSO which is subsequently oxidized to 3-(nitro-aryl) oxindole by DMSO.
- Sattar, Moh.,Rathore, Vandana,Prasad, Ch. Durga,Kumar, Sangit
-
supporting information
p. 734 - 743
(2017/04/13)
-
- Transition-Metal-Free C-H Hydroxylation of Carbonyl Compounds
-
Transition metal and reductant free α-C(sp3)-H hydroxylation of carbonyl compounds are reported. This method is promoted by commercially available inexpensive KO-t-Bu and atmospheric air as an oxidant at room temperature. This unified strategy is also very facile for hydroxylation of various carbonyl compound derivatives to obtain quaternary hydroxyl compounds in excellent yield. A preliminary mechanistic investigation, supported by isotope labeling and computational studies, suggests the formation of a peroxide bond and its cleavage by in situ generated enolate.
- Chaudhari, Moreshwar B.,Sutar, Yogesh,Malpathak, Shreyas,Hazra, Anirban,Gnanaprakasam, Boopathy
-
supporting information
p. 3628 - 3631
(2017/07/15)
-
- Manganese-Catalyzed Hydrogen-Autotransfer C?C Bond Formation: α-Alkylation of Ketones with Primary Alcohols
-
A novel catalytic hydrogen-autotransfer protocol for the atom-efficient α-alkylation of ketones with readily available alcohols is presented. The use of manganese complexes bearing non-innocent PNP pincer ligands enabled the functionalization of a broad range of valuable ketones, including 2-oxindole, estrone 3-methyl ether, and testosterone. Mechanistic investigations suggest the participation of an intramolecular amidate-assisted alcohol-dehydrogenation process.
- Pe?a-López, Miguel,Piehl, Patrick,Elangovan, Saravanakumar,Neumann, Helfried,Beller, Matthias
-
supporting information
p. 14967 - 14971
(2016/11/25)
-
- Pd/C-catalyzed alkylation of heterocyclic nucleophiles with alcohols through the "borrowing hydrogen" process
-
The alkylation of heterocyclic compounds is important for the synthesis of various biologically active compounds. In this paper, we present the development of a Pd/C-catalyzed alkylation of heterocyclic compounds using alcohols as the alkylating agents. T
- Putra, Anggi Eka,Oe, Yohei,Ohta, Tetsuo
-
p. 7799 - 7805
(2015/12/31)
-
- Reduction of 3-aminoquinoline-2,4(1H,3H)-diones and deamination of the reaction products
-
3-Aminoquinoline-2,4-diones were stereoselectively reduced with NaBH 4 to give cis-3-amino-3,4-dihydro-4-hydroxyquinolin-2(1H)-ones. Using triphosgene (=bis(trichloromethyl) carbonate), these compounds were converted to 3,3a-dihydrooxazolo[4,5-
- Klásek, Antonín,Ly?ka, Antonín,Rouchal, Michal,Rudolf, Ond?ej,R??i?ka, Ale?
-
p. 595 - 612
(2014/06/09)
-
- Regiodivergent access to five- and six-membered benzo-fused lactams: Ru-catalyzed olefin hydrocarbamoylation
-
We report herein a new strategy of the Ru-catalyzed intramolecular olefin hydrocarbamoylation for the regiodivergent synthesis of five- and six-membered benzo-fused lactams starting from N-(2-alkenylphenyl)formamides. Using a combined catalyst of Ru3
- Li, Bin,Park, Yoonsu,Chang, Sukbok
-
supporting information
p. 1125 - 1131
(2014/02/14)
-
- C-3 alkylation of oxindole with alcohols by Pt/CeO2 catalyst in additive-free conditions
-
In a series of transition metal-loaded CeO2 catalysts and Pt-loaded catalysts on various supports, Pt-loaded CeO2 shows the highest activity for the selective C-3 alkylation of oxindole with octanol. The catalyst is effective for alkylation of oxindole and N-substituted oxindole with a series of substituted benzyl, linear, hetero-aryl alcohols under additive-free conditions and is recyclable. Our results demonstrate the first additive-free catalytic system for this reaction. Mechanistic studies show that this system is driven by the borrowing-hydrogen pathway. Structure-activity relationship studies show that co-presence of surface Pt0 species on Pt metal clusters and basic support is indispensable for this catalytic system. This journal is the Partner Organisations 2014.
- Chaudhari, Chandan,Siddiki, S. M. A. Hakim,Kon, Kenichi,Tomita, Atsuko,Tai, Yutaka,Shimizu, Ken-Ichi
-
p. 1064 - 1069
(2014/04/03)
-
- Gold nanoparticles assisted formation of cobalt species for intermolecular hydroaminomethylation and intramolecular cyclocarbonylation of olefins
-
The intermolecular hydroaminomethylation and the intramolecular cyclocarbonylation efficiently proceeded on cobalt oxide supported gold nanoparticles. The intermolecular reaction employing terminal olefins and N-isopropylaniline afforded hydroaminomethylated products as a mixture of regioisomers via a common reaction path consisting of hydroformylation, imine formation, and hydrogenation. In contrast, indolinone derivatives were exclusively obtained in the case of 2-alkenylanilines based on the intramolecular cyclocarbonylation mechanism. Both of these reactions were catalyzed by cobalt species derived from cobalt oxide. The active cobalt species were formed via reduction of the oxide support promoted by deposited gold nanoparticles. Characterization of the catalysts before and after the reaction was also performed.
- Liu, Xiaohao,Hamasaki, Akiyuki,Yamane, Yoshihiro,Aikawa, Shohei,Ishida, Tamao,Haruta, Masatake,Tokunaga, Makoto
-
p. 3000 - 3006
(2013/11/06)
-
- A Facile Method for the Synthesis of 3-Alkyloxindole
-
Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.
- Du, Tai-Ping,Zhu, Gang-Guo,Zhou, Jian
-
p. 225 - 232
(2012/07/14)
-
- Organocatalytic enantioselective stereoablative hydroxylation of 3-halooxindoles: An effective method for the construction of enantioenriched 3-substituted 3-hydroxy-2-oxindoles
-
3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme).
- Liao, Yu-Hua,Wu, Zhi-Jun,Han, Wen-Yong,Zhang, Xiao-Mei,Yuan, Wei-Cheng
-
supporting information; experimental part
p. 8916 - 8920
(2012/10/08)
-
- Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis
-
Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a-g) exhibited an effective inhibitory activity on melanin synthesis. The Structure-Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30μM, IC50=1.40μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (-C=S, 3) to thiol (-C-SH, 4) led to decrease in the potency.
- Thanigaimalai, Pillaiyar,Lee, Ki-Cheul,Sharma, Vinay Kumar,Sharma, Niti,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
-
experimental part
p. 1285 - 1288
(2011/11/12)
-
- C-3 alkylation of oxindole with alcohols catalyzed by an indene-functionalized mesoporous iridium catalyst
-
A heterogeneous indene-based iridium catalyst with a highly ordered dimensional-hexagonal mesostructure was prepared through complexation of IrCl3 with the indene-functionalized SBA-15 silica materials. During C-3 alkylation of oxindole with va
- Liu, Guohua,Huang, Tianzeng,Zhang, Yuli,Liang, Xiaohui,Li, Yunsheng,Li, Hexing
-
experimental part
p. 655 - 659
(2012/01/12)
-
- Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols
-
A palladium complex sequentially promoted two mechanistically distinct reactions, the first, cyclization of 2-(alkynyl)aryl isocyanates with benzylic alcohols, and the second, [1,3] rearrangement of a benzyl group from oxygen to carbon, furnishing 3,3-dis
- Toyoshima, Takeharu,Mikano, Yusuke,Miura, Tomoya,Murakami, Masahiro
-
supporting information; experimental part
p. 4584 - 4587
(2010/12/25)
-
- Preparation of 3-alkyl-oxindoles by copper(II)-mediated C-H, Ar-H coupling followed by decarboxyalkylation
-
A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection. Georg Thieme Verlag Stuttgart - New York.
- Pugh, David. S.,Klein, Johannes E. M. N.,Perry, Alexis,Taylor, Richard J. K.
-
scheme or table
p. 934 - 938
(2010/07/16)
-
- Asymmetrie iminium ion catalysis with a novel bifunctional primary amine thiourea: Controlling adjacent quaternary and tertiary stereocenters
-
The development of a new bifunctional chiral primary amine thiourea catalyst and its application in the first asymmetric conjugate addition of oxindoles to enales was described. The reaction between 3-methyl oxindole and cinnamaldehyde, a combination of simple and readily available starting materials that targets in organic synthesis, was selected. The poor catalytic performance and the very low selectivity observed suggest a critical role of the thiourea moiety during the steroselective C-C bond-forming step. It is also found that by using 50% of benzoic acid, the catalyst loading is reduced to 10%, while still maintaining high diastero and enantiocontrol, and significant reactivity. The best diasterocontrol is observed for enals that have a naphthyl β substituted and by using oxindole that has a benzyl substitute.
- Galzerano, Patrizia,Bencivenni, Giorgio,Pesciaioli, Fabio,Mazzanti, Andrea,Giannichi, Berardino,Sambri, Letizia,Bartoli, Giuseppe,Melchiorre, Paolo
-
supporting information; experimental part
p. 7846 - 7849
(2010/03/31)
-
- Direct N-carbamoylation of 3-monosubstituted oxindoles with alkyl imidazole carboxylates
-
(Chemical Equation Presented) Regioselective N-carbamoylation of oxindoles was achieved through the use of imidazole carboxylate reagents. This reaction provides ready access to N-carbamoyl-3-monosubstituted oxindoles.
- Trost, Barry M.,Zhang, Yong,Zhang, Ting
-
supporting information; experimental part
p. 5115 - 5117
(2009/10/24)
-
- Highly enantioselective and organocatalytic α-amination of 2-Oxindoles
-
Figur Presented An effective method for the asymmetric synthesis of 3-amino-2-oxindoles was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of N-unprotected 2-oxindoles with azodicarboxylate catalyzed by commercial biscinchona alkaloids in good to excellent yields with high enantioselectivities.
- Cheng, Liang,Liu, Li,Wang, Dong,Chen, Yong-Jun
-
supporting information; experimental part
p. 3874 - 3877
(2009/12/06)
-
- Iridium catalysed C-3 alkylation of oxindole with alcohols under solvent free thermal or microwave conditions
-
Ir-catalysed alkylation of oxindole and N-methyl oxindole with a range of substituted benzyl and heteroaryl alcohols under solvent free thermal or microwave conditions afforded the corresponding C-3-monoalkylated products in high to excellent yield.
- Grigg, Ronald,Whitney, Simon,Sridharan, Visuvanathar,Keep, Ann,Derrick, Andrew
-
experimental part
p. 4375 - 4383
(2009/10/17)
-
- Ruthenium-catalyzed alkylation of oxindole with alcohols
-
(Chemical Equation Presented) An atom-economical and solvent-free catalytic procedure for the mono-3-alkylation of oxindole with alcohols is described. The reaction is mediated by the in situ generated catalyst from RuCl 3·xH2O and P
- Jensen, Thomas,Madsen, Robert
-
supporting information; experimental part
p. 3990 - 3992
(2009/12/25)
-
- Heterobimetallic cobalt/rhodium nanoparticle-catalyzed carbonylative cycloaddition of 2-alkynylanilines to oxindoles
-
(Chemical Equation Presented) The cobalt-rhodium heterobimetallic nanoparticle-catalyzed synthesis of oxindoles from 2-alkynylanilines in the presence of carbon monoxide is described.
- Park, Ji Hoon,Kim, Eunha,Chung, Young Keun
-
supporting information; experimental part
p. 4718 - 4721
(2009/05/31)
-
- New One-Pot Synthesis of 3-Alkyl- and 3-(ω-Hydroxyalkyl)oxindoles from Isatins
-
A new and efficient one-pot procedure has been developed for the synthesis of 3-alkyl- and 3-(ω-hydroxyalkyl)oxindoles from isatins by treatment with alcohols and diols in the presence of Raney nickel, under hydrogen atmosphere. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Volk, Balazs,Simig, Gyula
-
p. 3991 - 3996
(2007/10/03)
-
- Raney nickel-induced 3-alkylation of oxindole with alcohols and diols
-
New reaction conditions are described, which turn Wenkert's synthesis of 3-alkyloxindoles (Raney nickel-induced alkylation of oxindole with alcohols) into a reproducible and highly efficient synthetic tool. The method is also extended to the preparation o
- Volk, Balázs,Mezei, Tibor,Simig, Gyula
-
p. 595 - 597
(2007/10/03)
-
- Regioselective palladium(II)-catalyzed synthesis of five- or seven-membered ring lactones and five-, six- or seven-membered ring lactams by cyclocarbonylation methodology
-
2-Allylphenols react with carbon monoxide and hydrogen in the presence of catalytic quantities of a cationic palladium(II) complex [(PCy3)2Pd(H)(H2O)]+BF4- or palladium acetate and 1,4-bis(diphenylpho
- El Ali, Bassam,Okuro, Kazumi,Vasapollo, Giuseppe,Alper, Howard
-
p. 4264 - 4270
(2007/10/03)
-
- Rhodium-catalyzed carbonylation of 2-alkynylaniline: Syntheses of 1,3-dihydroindol-2-ones
-
Rhodium-catalyzed carbonylation of 2-alkynylanilines under water-gas shift reaction conditions gives 3-alkyl-1,3-dihydroindol-2-ones 2 in good yields along with a small amount of 2-quinolone derivatives 4. The reaction under carbonylation conditions witho
- Hirao, Kojiro,Morii, Noritsugu,Joh, Takashi,Takahashi, Shigetoshi
-
p. 6243 - 6246
(2007/10/02)
-
- Cyclization of N-Alkenyl-o-chloroanilides with Organonickel(0) Complexes: Conformational Analysis of 3-Substituted Oxindoles
-
3-substituted oxindoles (1)-(6) have been obtained as the main products of the cyclization reaction of N-alkenyl-o-chloroanilides with the zerovalent complex tetrakis(triphenylphosphine)nickel(0). 1H N.m.r. spectra of the oxindoles (2)-(6) show an AMX pro
- Rodriguez, J. Gonzalo,Canoira, Laureano,Temprano, Fernando
-
p. 1193 - 1196
(2007/10/02)
-
- Synthesis of Oxindole Derivatives from N-Alkenyl-o-Chloroanilides with Zero-Valent Nickel Complex
-
Oxindole derivatives have been obtained from N-alkenyl-o-chloroanilides by reaction with tetrakis(triphenylphoaphine)nickel(0) in toluene as solvent in good yields.A detailed analysis of all the products of the reaction allows to confirm the postulated mechanism of the cyclization reaction.The o-chloroanilides of the 3-cyclohexenylacetic acid fails in the cyclization reaction, since the torsional hindrance seems to avoid that the endocyclic double bond may be orthogonally to the ortho-?-nickel complex intermediate on the aromatic ring.
- Canoira, L.,Rodriguez, J. G.
-
p. 1511 - 1518
(2007/10/02)
-
- REGIOSELECTIVE C-3 ALKYLATIONS OF OXINDOLE DIANION
-
Oxindole is converted to its dianion by treatment with two equivalents each of n-BuLi and TMEDA.Alkylations with a number of common electrophiles define the scope of synthetically useful tramsformations leading to 3-monosubstituted and 3,3-disubstituted o
- Kende, Andrew, S.,Hodges, John C.
-
-