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1 dation undergoes further rearrangement to an oxindole.
2 in formation of an alpha,alpha-disubstituted oxindole.
3 ate molecules of the class isoindolinone and oxindole.
4 for the synthesis of chiral 3,3'-cyclopropyl oxindole.
5 shift on indole ring to ultimately produce 2-oxindole.
6 dominantly one enantiomer of the spirocyclic oxindole.
7 ucial and highly congested 3,3-disubstituted oxindole.
8 hods for the synthesis of 3,3'-disubstituted oxindoles.
9 eady access to N-carbamoyl-3-monosubstituted oxindoles.
10 aternary carbon in alpha,alpha-disubstituted oxindoles.
11 ioenriched N-unprotected 3-allyl-3-hydroxy-2-oxindoles.
12 ted spiro-pyrrolidinyl and spiro-piperidinyl oxindoles.
13 antioenriched spirocyclohexyl-indolines and -oxindoles.
14 ogically relevant quaternary carbon-centered oxindoles.
15 arious 5'-substituted spiro[pyrrolidine-3,3'-oxindoles].
16 d carbonate derivatives of the antirheumatic oxindole 1 were prepared and screened as potential prodr
20 variety of enantioenriched 3,3-disubstituted oxindoles 3 and spirolactones 4 were generated in modera
21 paraformaldehyde generates 3,3-disubstituted oxindoles 3 bearing a hydroxymethyl group, while the rea
22 ized symmetric/unsymmetric 3,3-disubstituted oxindole, 3-substituted 3-hydroxy oxindoles, 3,3-di(indo
23 ubstituted oxindole, 3-substituted 3-hydroxy oxindoles, 3,3-di(indolyl)indolin-2-ones, and a-aryl oxi
24 formation facilitate a rapid access to spiro[oxindole-3,2'-pyrrolidines] in their optically active fo
25 A novel stereocontrolled assembly of spiro[oxindole-3,2'-pyrrolidines] via [3+2]-cycloaddition of d
26 In this article, we have demonstrated that 2-oxindole-3-acetic acid (oxIAA) is a major primary IAA ca
27 oxidation of IAA to its primary catabolite 2-oxindole-3-acetic acid (oxIAA) remains uncharacterized.
28 ansform IAA into the biologically inactive 2-oxindole-3-acetic acid (oxIAA), representing a new bacte
29 d in Zea seedlings: Indole-3-acetic acid --> Oxindole-3-acetic acid --> 7-Hydroxyoxindole-3-acetic ac
30 t is present at levels comparable to that of oxindole-3-acetic acid and indole-3-acetic acid (62 pico
33 ific showing no glucose ester formation with oxindole-3-acetic acid or 7-hydroxy-oxindole-3-acetic ac
36 ion with oxindole-3-acetic acid or 7-hydroxy-oxindole-3-acetic acid, and low activity with phenylprop
40 l diazoesters 3, and acrylic ester/3-alkenyl oxindoles 5/6 provide various dihydroindolizines 7 to 9
42 owth factor receptor 1 kinase inhibitor) and oxindole (a vascular endothelial growth factor receptor
46 between the E and Z isomers of the starting oxindoles allowed a site-specific diastereoselective and
47 terestingly, (E)-3-(2-(aryl)-2-oxoethylidene)oxindole and (E)-3-ylidene oxindole give different diast
49 kylidene)indolin-2-ones in high yield from 2-oxindole and aryl/alkyl nitrile in the presence of LiOtB
50 s achieved by protecting the N-center of the oxindole and C5 alkylated product is furnished exclusive
54 are broad in scope with respect to both the oxindole and nitroolefin substrates and provide the desi
56 hibited that two of the suitably substituted oxindole and triazatuxene may have atropisomerism at roo
58 loped by employing 3-(2-oxo-2-arylethylidene)oxindoles and 1,4-benzoxazinone as starting materials.
59 atile route to enantiopure 3,3-disubstituted oxindoles and 3a-substituted pyrrolidinoindolines is des
60 liver direct access to 3-allyl-3-aminomethyl oxindoles and 5-silyl methyl spiro[pyrrolidine-3,3'-oxin
62 ectivity for a variety of unprotected 3-aryl oxindoles and benzylic methyl carbonates using chiral bi
63 construction of a C-C bond between 3-ylidene oxindoles and electron-rich arenes has been successfully
64 ion to engineer TrpB to accept 3-substituted oxindoles and form C-C bonds leading to new quaternary s
65 ethod provides access to 3-(fluoromethylene) oxindoles and gamma-lactams with excellent stereoselecti
66 ect construction of a range of spirocyclized oxindoles and indolenines in good to excellent yields.
67 report the palladium-catalyzed reactions of oxindoles and indoles, both functioning as bis-nucleophi
68 cturally diverse and valuable functionalized oxindoles and isoquinolinediones in moderate to good yie
69 selective domino reactions of spiroaziridine oxindoles and malononitrile have been developed using DB
70 Michael-aldol reaction between 3-substituted oxindoles and methyleneindolinones that affords complex
72 lopentannulation has been devised, employing oxindoles and pyrazolones as prototypical platforms.
74 s of biologically active 3,3-bis(hydroxyaryl)oxindoles and spirooxindoles bearing a xanthene moiety.
76 in activity for alkylation of 3-substituted oxindoles and the ability to selectively form a new, all
79 d indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in
80 ore was accomplished in 13 steps using a new oxindole annulation and late-stage enamine oxidation.
81 ict an isatin-derived and 3,3'-disubstituted oxindole-appended epoxy-acrylate undergoing Cp(2)Ti(III)
83 ric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization pr
87 icle describes our work regarding the use of oxindoles as carbon-based nucleophiles in a Pd-catalyzed
88 esent the first ever use of 3-isopropylidene oxindoles as electrophiles in vinylogous Michael initiat
91 s, 3,3-di(indolyl)indolin-2-ones, and a-aryl oxindoles as valuable building blocks is further illustr
92 the late-stage diversification of bioactive oxindoles as well as facilitated the synthesis of quinol
93 ed catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exc
94 eloped a stereochemically paired spirocyclic oxindole aziridine covalent library and screened this li
96 Walter Reed chemical database, we identified oxindole-based compounds as effective inhibitors of Pfmr
98 proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaterna
99 cedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers in
101 N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is rep
104 ion-metal-free method to construct N-hydroxy oxindoles by an aza-Nazarov-type reaction involving azao
105 od to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxin
106 hree-dimensional (3D) polyheterocyclic spiro-oxindoles by Lewis-acid-catalyzed Friedel-Crafts type C-
107 esis of beta-pyridone-alpha,beta-unsaturated oxindoles by the reaction of isatins and 2-chloropyridin
108 synthesizing a series of 3-functionalized 2-oxindoles by varying the isatin, amine, and alcohol comp
109 atalyst system, the corresponding 3-arylated oxindoles can be obtained in good to excellent yields (<
110 tion partners such as N-protected alkylidene oxindole carboxylates and pyridinium ylides to afford na
111 al benzylic ether serves as an auxiliary for oxindole carboxylation (dr 5.2:1.0) that sets C10 config
112 tive alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine liga
113 ly provided a similar yield of 3-arylidene-2-oxindoles compared with more reactive aryl iodides.
114 bitors led to novel, chemically stable spiro-oxindole compounds bearing a spiro[3H-indole-3,2'-pyrrol
115 hane at 70 C, affords 3-alkyl-3-(hydroxyaryl)oxindole compounds with a high degree of selectivity.
116 s, whereas the moieties that extend from the oxindole contact residues in the hinge region between th
117 atalyst derived from Pd(OAc)(2) to construct oxindoles containing a diaryl-substituted all-carbon qua
118 OCl(3)-mediated direct cyclotrimerization of oxindoles containing electron-deficient substituents on
119 in the formation of 2-chloroindoles, whereas oxindoles containing electron-donating substituents gave
124 ry carbon center are derived from alkylidene oxindole, coumarin, and malonate substrates with high st
125 rated challenging (i.e., alpha-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azl
127 ymmetric organocatalytic cascade reaction of oxindole derivates with a,B-unsaturated aldehydes effici
129 biologically important phenol-substituted 2-oxindole derivatives directly without any skeleton rearr
131 -free catalytic system providing a series of oxindole derivatives having two contiguous stereocenters
133 bstrates led to the formation of spirocyclic oxindole derivatives in good yields with complete regios
138 iourea-catalyzed asymmetric 1,4-additions of oxindole derivatives to nitroolefins as a key step.
139 were used under mild conditions to construct oxindole derivatives with high enantiopurity and structu
142 nge of enantioenriched spiro[3,2'-morpholine-oxindole] derivatives which incorporate a tertiary stere
143 orts an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane eff
144 iodinated hetero- and carbocycles including oxindoles, dihydrobenzofurans, indolines, a chromane, an
147 The competing reactivity of isopropylidene oxindoles (electrophilicity vs nucleophilicity) in the p
148 cient direct alkynylations of 3-alkyl/aryl 2-oxindoles employing ethynyl-1,2-benziodoxol-3(1H)-one (E
150 such as an intriguing propellane hexacyclic oxindole encountered in the communesin F sequence, are d
152 e diones are tricyclic N-acyl-2-alkylidene-3-oxindole enones that readily engage in tertiary phosphin
154 onalities and the formation of 3-fluorinated oxindoles exhibiting an array of four adjacent centers o
155 rmolytic skeletal rearrangement of 3-azide-2-oxindole for the synthesis of biologically important qui
156 heme-dependent enzyme, catalyzes a unique 2-oxindole-forming monooxygenation reaction from tryptopha
158 igh-throughput crystallography identified an oxindole fragment bound to the S1 pocket of the protein
159 enantiomer and-as the reaction progresses-by oxindole fragmentation products blocking the binding sit
161 he selective functionalization of indole and oxindole frameworks employing an alternative strategy in
162 thod for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using
164 ll-carbon tetrasubstituted olefin containing oxindoles from readily accessible anilides has been deve
165 )-2-oxoethylidene)oxindole and (E)-3-ylidene oxindole give different diastereomers on nitration.
167 The synthesis of dihydrobenzofuran-appended oxindoles has been accomplished taking advantage of an u
168 elective, one-pot synthesis of 3-arylidene-2-oxindoles has been accomplished via Heck-like carbocycli
169 of symmetrical and unsymmetrical 3-arylidene oxindoles has been described from diazoindolones and dip
172 Pathways for direct conversion of indoles to oxindoles have accumulated considerable interest in rece
173 w anticancer therapeutic strategy, and spiro-oxindoles have been designed as a class of potent and ef
174 linear and cross-conjugated trienamines with oxindoles have been studied with density functional theo
185 access to novel spiro-dihydronaphthoquinone-oxindoles in excellent yields with complete selectivity
187 complex by azoles afforded 3,3-disubstituted oxindoles in good yields with excellent enantioselectivi
188 the synthesis of a wide range of 3-alkenyl-2-oxindoles in good yields with excellent functional group
189 diverse 1,3-diazaspiro[bicyclo[3.1.0]hexane]oxindoles in isolated yields up to 81% under mild condit
193 al of these, including 4-ethylphenylsulfate, oxindole, indolepropionate, p-cresol sulfate, catechol s
194 own to provide direct access to an important oxindole intermediate, could be applied to the total syn
195 nother transformation of 3-(nitroalkylidene) oxindole into 3-(tosylalkylidene) oxindole was performed
199 ichael addition of nitroalkanes to 3-ylidene oxindoles is described, mediated by thiourea-based bifun
201 y C3-(sp(3)-carbon) center of spiroaziridine oxindoles is developed using inexpensive trimethylsilyl
203 o quaternary C-acetylated and C-carboxylated oxindoles is observed, even for substrates containing br
204 amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording
205 catalyzed multicomponent reaction of 3-diazo oxindole, isocyanide, and aniline has been developed.
206 by employing differently substituted 3-diazo oxindoles, isocyanides, and anilines as starting materia
208 ic compounds containing amide, indanone, and oxindole moieties in good to excellent yields with high
209 nd allows for the direct introduction of the oxindole moiety onto a range of aromatic compounds inclu
210 key feature of these molecules is the spiro-oxindole moiety that lends a strained three-dimensional
211 ive cyclization of an N-Boc aniline onto the oxindole moiety to form a pentacyclic framework containi
212 , efficient, and sustainable generation of 2-oxindole motifs, which are already known for a plethora
216 catalyzed sequential Michael addition of bis-oxindole onto nitroethylene (up to 93% ee and >20:1 dr).
217 s wherein the first nucleophilic unit on the oxindole or indole reacts with an allenyl-palladium spec
220 s, such as N-CF(3) decorated alkenyl amides, oxindoles, or quinolones, all of which were inaccessible
223 y, the variants that could use 3-substituted oxindoles preferentially formed N-C bonds on N(1) of the
225 xazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee.
226 olyheterocycles are skillfully embraced with oxindole, pyrrole, and coumarin scaffolds, which are wel
227 llows the formation of chiral bispirocyclic [oxindole-pyrrolidine-pyrazolones] in high yields (up to
228 An initial subdeck screen revealed that the oxindole-pyrrolo[2,1- f][1,2,4]triazine lead 2a displaye
230 ylides of 1,3-dicarbonyls and 3-alkylidene-2-oxindoles results in 3H-spiro[furan-2,3'-indolin]-2'-one
231 Heck cyclization for the installation of the oxindole ring system as well as a directed hydrosilylati
235 it has been developed for the synthesis of 2-oxindoles sharing vicinal all-carbon quaternary stereoce
236 xperiments using enantioenriched 3-hydroxy-2-oxindole show that the reaction proceeds through in situ
237 n the synthesis of a short library of chiral oxindoles, showing activity almost comparable to that of
238 ess to novel spiropyrrolo[1,2-a]isoquinoline-oxindole skeletons by a one-pot three-component [3 + 2]
239 s such as 3-spiro[1-azabicyclo[3.2.0]heptane]oxindoles spiro-conjugated or fused to a succinimide moi
243 C-H functionalization event involving a keto oxindole substrate to introduce the tetrahydrofuran ring
246 changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer rea
248 les in a Pd-catalyzed asymmetric addition of oxindoles to allenes (Pd-catalyzed hydrocarbonation of a
251 of diverse heterocycles onto spirocyclobutyl oxindoles under mild, operationally simple conditions, m
252 owed that some of our first-generation spiro-oxindoles undergo a reversible ring-opening-cyclization
253 Further, it provides an opportunity to merge oxindole units with clinically used drugs like norethind
255 selective azidations of beta-keto esters and oxindoles using a readily available N3-transfer reagent
256 ckel-catalyzed C-3-selective alkylation of 2-oxindoles using a wide variety of secondary alkyl alcoho
257 or the union of amides, imides, ketones, and oxindoles using soluble copper(II) or iron(III) salts as
258 rted for the synthesis of 3-(aminoalkylidene)oxindoles via a sequential condensation-hydrolysis- nucl
259 ure for the synthesis of 3,3-disubstituted 2-oxindoles via cross-dehydrogenative coupling (CDC) is re
260 demanding unsymmetrical 3,3-disubstituted 2-oxindoles via reductive cyclization of alpha-ketoamides
261 ployed to synthesize 3-amino- and 3-triazole oxindoles via Staudinger reduction and click chemistry,
262 he cascade transformation of 3-(2-azidoethyl)oxindoles via Staudinger/aza-Wittig/Mannich reactions.
263 lkylidene) oxindole into 3-(tosylalkylidene) oxindole was performed through metal and oxidant-free to
265 biologically relevant spiro-dihydropyridine oxindoles was described via readily available isatin, ma
267 biologically relevant spiro[pyrrolidine-3,3'-oxindoles] was developed on the basis of the cascade tra
268 to a stereogenic carbon and an N-coordinated oxindole were synthesized by the reaction of alkenyl ary
270 zine]- and 3-spiro[3-azabicyclo[3.1.0]hexane]oxindoles were prepared in moderate to high yields via o
273 and selective synthesis of (E)-3-alkylidene oxindole, which is a highly valuable framework due to it
274 trated in the synthesis of 3,3-disubstituted oxindoles, which are prevalent motifs seen in numerous b
277 his transformation allows the preparation of oxindoles with a quaternary carbon stereocenter using no
278 formal [3 + 2]-annulation of spiro-aziridine oxindoles with allylsilanes have been demonstrated to de
279 for the allylation reactions of 3-hydroxy-2-oxindoles with allyltrimethylsilane has been developed.
280 the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst s
283 tions for the exclusive synthesis of 3-azido oxindoles with excellent yield and enantioselectivity (e
284 uted highly enantioenriched spirocyclopropyl oxindoles with excellent yield and stereoselectivities.
285 ee conditions afforded 3-allyl-3-aminomethyl oxindoles with good stereoselectivity (ee up to 80%).
288 rein we disclose a novel aminooxygenation of oxindoles with nitrosobenzene catalyzed by a newly desig
289 annulative coupling of spirovinylcyclopropyl oxindoles with p-quinone methides has been accomplished
292 thesized a series of second-generation spiro-oxindoles with symmetrical pyrrolidine C2 substitution.
293 ation of the beta C-H bond of 3-alkylidene-2-oxindoles with tert-butyl nitrite (TBN) has been explore
294 construct a C-O bond at the C(3) position of oxindoles with the creation of an oxygen-containing tetr
295 tion unpredictably affords 3,3-disubstituted oxindoles with the formal reduction of the nitro group u
297 e 3,4-dihydrospiro[benzo[b][1,4]oxazine-2,3'-oxindole] with excellent enantiopurity (ee up to >99%).