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1.
A novel approach to diversely functionalized spirocyclic oxindoles has been developed by using different metal-mediated carbonyl-addition/cyclization reaction sequences. Spirocyclization precursors, 2-indolinone-tethered homoallylic alcohols, (buta-1,3-dien-2-yl)methanols, and alpha-allenols have been obtained by regioselective addition of stabilized organoindium reagents to isatins in aqueous environment. Ruthenium-, silver-, and palladium-catalyzed reactions of the above unsaturated alcohol derivatives provided oxaspiro oxindoles. 相似文献
2.
Márta Porcs-Makkay Balázs Volk Rita Kapiller-Dezsófi Tibor Mezei Gyula Simig 《Monatshefte für Chemie / Chemical Monthly》2004,26(5):697-711
A new, practical synthesis of the antirheumatic oxindole derivative, tenidap, has been elaborated. The new approach has initiated studies on the mechanism of the acylation reactions of oxindoles. Methods have been developed for the synthesis of 1-[alkoxy(or aryloxy)carbonyl]- and 1,3-di[alkoxy(or aryloxy)carbonyl]oxindoles starting from oxindoles. The route designed for tenidap has provided a facile access to several analogues, too.On another front, new reaction conditions are described, which turn Wenkerts synthesis of 3-alkyloxindoles (by Raney nickel induced alkylation of oxindoles with alcohols) into a highly efficient synthetic tool. The method has been extended to the synthesis of 3-alkyloxindoles from isatins and to the preparation of 3-(-hydroxyalkyl)oxindoles from oxindoles and isatins. 相似文献
3.
Summary. A new, practical synthesis of the antirheumatic oxindole derivative, tenidap, has been elaborated. The new approach has initiated studies on the mechanism of the acylation reactions of oxindoles. Methods have been developed for the synthesis of 1-[alkoxy(or aryloxy)carbonyl]- and 1,3-di[alkoxy(or aryloxy)carbonyl]oxindoles starting from oxindoles. The route designed for tenidap has provided a facile access to several analogues, too.On another front, new reaction conditions are described, which turn Wenkerts synthesis of 3-alkyloxindoles (by Raney nickel induced alkylation of oxindoles with alcohols) into a highly efficient synthetic tool. The method has been extended to the synthesis of 3-alkyloxindoles from isatins and to the preparation of 3-(-hydroxyalkyl)oxindoles from oxindoles and isatins. 相似文献
4.
Zhao-Zhao Zhou Hui-Liang Hua Jian-Yi Luo Zi-Sheng Chen Ping-Xin Zhou Xue-Yuan Liu Yong-Min Liang 《Tetrahedron》2013
Metal-free synthesis of 3,3-disubstituted oxindoles utilizing N-arylacrylamides and simple alcohols is developed. It provides an efficient method for preparing a series of hydroxyl-containing oxindole derivatives. This reaction is proposed to proceed through oxidative radical cyclization mechanism. The remarkable features of the reaction are metal-free condition and excellent functional group tolerance. 相似文献
5.
A unique one-pot cyclization of 2-aminophenethyl alcohols with carboxylic acids in the presence of PPh3, CCl4, and NEt3 furnished the formation of N-acyl indolines in good to excellent yields. This new approach provides an efficient, scalable, low-cost, and direct access to the biologically important indolines which are further oxidizable to indoles and oxindoles. 相似文献
6.
I. V. Dlinnykh G. A. Golubeva I. F. Leshcheva V. V. Nesterov M. Yu. Antipin L. A. Sviridova 《Chemistry of Heterocyclic Compounds》2004,40(9):1142-1149
The reaction of oxindoles with 5-hydroxypyrazolidines on the surface of potassium fluoride-modified alumina leads to 3-(5-pyrazolidinyl)oxindoles. The structure of these products was studied. 相似文献
7.
A Divergent Approach to the Diastereoselective Synthesis of 3,3‐Disubstituted Oxindoles from Atropisomeric N‐Aryl Oxindole Derivatives 下载免费PDF全文
Dr. Atsuo Nakazaki Ayako Mori Prof. Dr. Susumu Kobayashi Prof. Dr. Toshio Nishikawa 《化学:亚洲杂志》2016,11(22):3267-3274
3,3‐Disubstituted oxindoles were divergently synthesized by diastereoselective transformations including nucleophilic addition, alkylation, and cycloaddition using common, axially chiral N‐aryl oxindoles. Notably, high diastereoselectivities (up to >95:5) were observed with ortho‐monosubstituted N‐aryl oxindoles to give various oxindole scaffolds, and facile removal of the p‐(benzyloxy)aryl moiety in axially twisted amides was achieved by a mild, two‐step sequence. 相似文献
8.
Atsuo Nakazaki Ayako Mori Susumu Kobayashi Toshio Nishikawa 《Tetrahedron letters》2012,53(52):7131-7134
Diastereoselective synthesis of 3,3-disubstituted oxindoles has been examined by transformations involving nucleophilic addition, alkylation, and cycloaddition using chiral racemic N-aryl oxindoles bearing C–N axial chirality. The most striking features of this approach are high diastereoselectivities (up to >95:<5) when using ortho-monosubstituted N-aryl oxindoles and easy removal of the p-(benzyloxy)aryl moiety in the axially twisted amides by a mild two-step sequence. 相似文献
9.
MagedK.G. Mekhael Stefan Bienz Anthony Linden Heinz Heimgartner 《Helvetica chimica acta》2004,87(9):2385-2404
A novel general method for the synthesis of oxindoles, namely the ‘azirine/oxindole ring enlargement via amidinium‐intermediates’ has been established: the reaction of 2H‐azirin‐3‐amines 1 with BF3?OEt2 in THF solution at ?78° leads to 1,3,3‐trialkyl‐2‐amino‐3H‐indolium tetrafluoroborates 14 in good yields (Scheme 5). Treatment of aqueous solutions of 14 at 0° with aqueous NaOH (30%) and extraction with CH2Cl2 gives oily substances that are either hydrates of 1,3,3‐trialkyl‐2‐dihydroindol‐2‐imines 15 or the corresponding indolium hydroxides. These products are transformed to the corresponding 1,3,3‐trialkyl‐2,3‐dihydroindol‐2‐ones 17 in modest yields upon refluxing in H2O/THF. Reaction of 14 with Ac2O in pyridine at ca. 23° for 16 h followed by aqueous workup and chromatographic separation leads to mixtures of N‐(1,3,3‐trialkyl‐2,3‐dihydro‐indol‐2‐yliden)acetamides 16 and oxindoles 17 (Scheme 6). Hydrolysis of 16 with aqueous HCl under reflux for 1–2 h gives oxindoles 17 in a good yield. Several oxindoles, spiro‐oxindoles, and 5‐substituted oxindoles were synthesized by means of the reactions mentioned above. 相似文献
10.
Ming Chen Xucai Wang Pengfei Yang Xun Kou Zhi-Hui Ren Prof. Dr. Zheng-Hui Guan 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(29):12297-12303
Reported herein is the development of the first enantioselective monodentate ligand assisted Pd-catalyzed domino Heck carbonylation reaction with CO. The highly enantioselective domino Heck carbonylation of N-aryl acrylamides and various nucleophiles, including arylboronic acids, anilines, and alcohols, in the presence of CO was achieved. A novel monodentate phosphoramidite ligand, Xida-Phos, has been developed for this reaction and it displays excellent reactivity and enantioselectivity. The reaction employs readily available starting materials, tolerates a wide range of functional groups, and provides straightforward access to a diverse array of enantioenriched oxindoles having β-carbonyl-substituted all-carbon quaternary stereocenters, thus providing a facile and complementary method for the asymmetric synthesis of bioactive hexahydropyrroloindole and its dimeric alkaloids. 相似文献
11.
Yu‐Hua Liao Xiong‐Li Liu Dr. Zhi‐Jun Wu Prof. Xi‐Lin Du Prof. Dr. Xiao‐Mei Zhang Prof. Dr. Wei‐Cheng Yuan 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(21):6679-6687
An asymmetric conjugate addition of 3‐monosubstituted oxindoles to a range of (E)‐1,4‐diaryl‐2‐buten‐1,4‐diones, catalyzed by commercially available cinchonine, is described. This organocatalytic asymmetric reaction affords a broad range of 3,3′‐disubstituted oxindoles that contain a 1,4‐dicarbonyl moiety and vicinal quaternary and tertiary stereogenic centers in high‐to‐excellent yields (up to 98 %), with excellent diastereomeric and moderate‐to‐high enantiomeric ratios (up to 99:1 and 95:5, respectively). Subsequently, cyclization of the 1,4‐dicarbonyl moiety in the resultant Michael adducts under different Paal–Knorr conditions results in two new kinds of 3,3′‐disubstituted oxindoles—3‐furanyl‐ and 3‐pyrrolyl‐3‐alkyl‐oxindoles—in high yields and good enantioselectivities. Notably, the studies presented here sufficiently confirm that this two‐step strategy of sequential conjugate addition/Paal–Knorr cyclization is not only an attractive method for the indirect enantioselective heteroarylation of 3‐alkyloxindoles, but also opens up new avenues toward asymmetric synthesis of structurally diverse 3,3′‐disubstituted oxindole derivatives. 相似文献
12.
Hui Qin Yuanyuan Miao Ke Zhang Jian Xu Haopeng Sun Wenyuan Liu Feng Feng Wei Qu 《Tetrahedron》2018,74(47):6809-6814
A practical convenient conversion of oxindoles into the corresponding spirocyclopropyl oxindoles is achieved efficiently using bromoethylsulfonium salt, which is easily prepared on a large scale and is stable crystalline. This reaction of bromoethylsulfonium salt with different substituted unprotected oxindoles proceeded under mild condition and provided moderate yields. 相似文献
13.
Ming Chen Xucai Wang Pengfei Yang Xun Kou Zhi‐Hui Ren Zheng‐Hui Guan 《Angewandte Chemie (International ed. in English)》2020,59(29):12199-12205
Reported herein is the development of the first enantioselective monodentate ligand assisted Pd‐catalyzed domino Heck carbonylation reaction with CO. The highly enantioselective domino Heck carbonylation of N‐aryl acrylamides and various nucleophiles, including arylboronic acids, anilines, and alcohols, in the presence of CO was achieved. A novel monodentate phosphoramidite ligand, Xida‐Phos, has been developed for this reaction and it displays excellent reactivity and enantioselectivity. The reaction employs readily available starting materials, tolerates a wide range of functional groups, and provides straightforward access to a diverse array of enantioenriched oxindoles having β‐carbonyl‐substituted all‐carbon quaternary stereocenters, thus providing a facile and complementary method for the asymmetric synthesis of bioactive hexahydropyrroloindole and its dimeric alkaloids. 相似文献
14.
15.
Liao YH Wu ZJ Han WY Zhang XM Yuan WC 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(29):8916-8920
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). 相似文献
16.
Jie Liu Shubhadip Mallick Yusheng Xie Corentin Grassin Belén Lucas Beate Schölermann Axel Pahl Rebecca Scheel Carsten Strohmann Christoph Protzel Thorsten Berg Christian Merten Slava Ziegler Herbert Waldmann 《Angewandte Chemie (International ed. in English)》2023,62(21):e202301955
Oxindoles and iso-oxindoles are natural product-derived scaffolds that provide inspiration for the design and synthesis of novel biologically relevant compound classes. Notably, the spirocyclic connection of oxindoles with iso-oxindoles has not been explored by nature but promises to provide structurally related compounds endowed with novel bioactivity. Therefore, methods for their efficient synthesis and the conclusive discovery of their cellular targets are highly desirable. We describe a selective RhIII-catalyzed scaffold-divergent synthesis of spirooxindole–isooxindoles and spirooxindole–oxindoles from differently protected diazooxindoles and N-pivaloyloxy aryl amides which includes a functional group-controlled Lossen rearrangement as key step. Unbiased morphological profiling of a corresponding compound collection in the Cell Painting assay efficiently identified the mitotic kinesin Eg5 as the cellular target of the spirooxindoles, defining a unique Eg5 inhibitor chemotype. 相似文献
17.
Asymmetric synthesis plays an important role in the synthesis of therapeutics and natural products. Asymmetric oxindoles with a stereogenic quaternary carbon center are extensively present in various natural products and biologically active compounds. Several methods such as employing chiral auxiliaries or chiral catalysts were developed for asymmetric synthesis of spirooxindoles or 3,3-disubtituted oxindoles. In this review, we make a detailed overview of the latest developments in the use of isatin as starting material for the asymmetric synthesis of spirooxindoles and 3,3-disubstituted oxindoles during the period from 2015 to 2017. 相似文献
18.
研究了手性磷酸催化的靛红衍生酮亚胺与噁唑酮的不对称Mannich型加成反应, 以良好至优秀的收率(高达97%)、 对映选择性(高达99% e.e.)以及非对映选择性(均>20∶1 d.r.)得到一系列含噁唑酮骨架的手性3,3′-二取代氧化吲哚化合物. 该反应可以进行扩大化和衍生反应. 相似文献
19.
A Metal‐free Approach to 3‐Aryl‐3‐hydroxy‐2‐oxindoles by Treatment of 3‐Acyloxy‐2‐oxindoles with Diaryliodonium Salts 下载免费PDF全文
A mild, metal‐free approach has been realized for the facile construction of highly valuable 3‐(hetero)aryl‐3‐hydroxy‐2‐oxindoles. Direct arylations of 3‐acyloxy‐2‐oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K2CO3 at room temperature without using an organometallic promoter to deliver an array of 3‐(hetero)aryl‐3‐hydroxy‐2‐oxindoles in good yields. 相似文献
20.
Remote Construction of Chiral Vicinal Tertiary and Quaternary Centers by Catalytic Asymmetric 1,6‐Conjugate Addition of Prochiral Carbon Nucleophiles to Cyclic Dienones 下载免费PDF全文
Yuan Wei Zunwu Liu Xinxin Wu Jie Fei Xiaodong Gu Xiaoqian Yuan Prof. Dr. Jinxing Ye 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(52):18921-18924
An unprecedented remote construction of chiral vicinal tertiary and quaternary centers by a catalytic asymmetric 1,6‐conjugate addition of prochiral carbon nucleophiles to cyclic dienones has been developed. Both 5H‐oxazol‐4‐ones and 2‐oxindoles were found to be very efficient carbon nucleophiles in this reaction at a remote position, giving products with excellent enantio‐ and diastereoselectivities (up to 99 % ee and >19:1 d.r. for 5H‐oxazol‐4‐ones and up to 97 % ee and >19:1 d.r. for 2‐oxindoles). 相似文献