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1.
《Journal of heterocyclic chemistry》2017,54(2):1479-1485
A formal [3 + 2] cyclization reaction of 3‐(2‐oxo‐2‐arylethylidene)indolin‐2‐ones and amidines has been developed, regioselectively affording a series of new 3‐(imidazol‐4‐yl)indolin‐2‐ones in good to excellent yields. The reaction was easily conducted in ethylene glycol using Cs2CO3 as a base promoter under microwave irradiation. Flexible structural modification, and broad functional group compatibility as well as mild reaction conditions make this strategy a useful and attractive process of library generation for drug discovery. 相似文献
2.
N‐Heterocyclic Carbene‐Catalyzed Enantioselective Annulation of Indolin‐3‐ones with Bromoenals
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Qijian Ni Xiaoxiao Song Prof. Dr. Gerhard Raabe Prof. Dr. Dieter Enders 《化学:亚洲杂志》2014,9(6):1535-1538
N‐Heterocyclic carbene‐catalyzed reactions of indolin‐3‐ones with 2‐bromoenals opened an asymmetric access to 3,4‐dihydropyrano[3,2‐b]indol‐2(5 H)‐ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented. 相似文献
3.
Dr. Prasath Kothandaraman Bing Qin Koh Dr. Taweetham Limpanuparb Prof. Dr. Hajime Hirao Prof. Dr. Philip Wai Hong Chan 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(6):1978-1985
A synthetic method that relies on NIS (N‐iodosuccinimide)‐mediated cycloisomerization reactions of 1‐(2′‐anilinyl)prop‐2‐yn‐1‐ols to gem‐3‐(diiodomethyl)indolin‐2‐ones and 2‐(iodomethylene)indolin‐3‐ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3‐ and 2‐oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2‐OH and 1,2‐alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. 相似文献
4.
《Journal of heterocyclic chemistry》2017,54(2):1450-1456
The reaction of 3‐(3‐amino‐5‐oxo‐1,5‐dihydropyrazol‐4‐ylidene)‐1,3‐dihydroindol‐2‐one with N‐aryl‐2‐oxopropane hydrazonoyl chlorides in dioxane in the presence of triethylamine proceeded regio‐ and site selectively to give 3‐(2‐arylazo‐3‐methyl‐6‐oxo‐imidazo[1,2‐b ]pyrazol‐7‐ylidene‐indol‐2‐ones rather than the isomeric form 3‐(3‐arylazo‐2‐methyl‐6‐oxo‐imidazo[1,2‐b ]pyrazol‐7‐ylidene‐indol‐2‐ones. On the other hand, the reaction of N ’‐(2‐oxoindoline‐3‐ylidene)hydrazinecarbothiohydrazide with hydrazonoyl chlorides in refluxing ethanol and in the presence of triethylamine proceeded regio‐ and site selectively to give the respective 3‐(substituted‐1,3,4‐thiadiazol‐2‐ylidenehydrazono)indolin‐2‐ones. The mechanism of formation of the new products was also discussed. The structure assigned for the products was established by elemental and spectral data (1H‐NMR, IR, and Mass) and NOE experiment. Moreover, the biological activity of the products was evaluated against some fungi and bacteria, and the results obtained revealed the high potency of some of them compared with the used standard references. 相似文献
5.
Sreedhar Maroju Naveen Kumar Podila Ganapathi Velupula Srinivasulu Chittimalla T. Ravi Pasad 《Journal of heterocyclic chemistry》2019,56(1):153-157
Ten compounds of new (Z)‐5‐((1H‐1,24‐triazol‐1‐yl)methyl)‐3‐arylideneindolin‐2‐ones ( 5a – j ) have been synthesized by the Knoevenagel condensation of 5‐((1H‐1,2,4‐triazol‐1‐ylmethyl)indolin‐2‐one ( 3 ) with 4‐substituted aromatic aldehydes ( 4a – j ). 相似文献
6.
Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin‐3‐ones Bearing Quaternary Stereocenters
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Dr. Ren‐Rong Liu Shi‐Chun Ye Dr. Chuan‐Jun Lu Dr. Gui‐Lin Zhuang Prof. Dr. Jian‐Rong Gao Prof. Dr. Yi‐Xia Jia 《Angewandte Chemie (International ed. in English)》2015,54(38):11205-11208
The enantioselective redox annulation of nitroalkynes with indoles is enabled by gold/chiral phosphoric acid dual catalysis. A range of indolin‐3‐one derivatives bearing quaternary stereocenters at the C2 position were afforded in good yields and excellent enantioselectivities (up to 96 % ee) from readily available starting materials. 相似文献
7.
Ren‐Ming Hu Dong‐Yang Han Ning Li Jie Huang Yu Feng Da‐Zhen Xu 《Angewandte Chemie (International ed. in English)》2020,59(10):3876-3880
Presented herein is the first direct alkylation and hydroxylation reaction between two different C(sp3)?H bonds, indolin‐2‐ones and alkyl‐substituted N‐heteroarenes, through an oxidative cross‐coupling reaction. The reaction is catalyzed by a simple iron salt under mild ligand‐free and base‐free conditions. The reaction is environmentally benign, employs air (molecular oxygen) as the terminal oxidant and oxygen source for the synthesis of O‐containing compounds, and produces only water as the byproduct. 相似文献
8.
John Spencer Birthe V. Nielsen Michael J. K. Thomas Louise Male Simon J. Coles 《Acta Crystallographica. Section C, Structural Chemistry》2011,67(7):m245-m248
Indolin‐2‐one (oxindole), (I), undergoes a Knoevenagel condensation with ferrocene‐1,1′‐dicarbaldehyde, (II), to afford the title complex 3,3′‐[(E,E)‐ferrocene‐1,1′‐diyldimethylidyne]diindolin‐2‐one dichloromethane disolvate, [Fe(C28H20N2O2)]·2CH2Cl2, (IV). The structure of (IV) contains two ferrocene complex molecules in the asymmetric unit and displays, as expected, intermolecular hydrogen bonding (N—H...O=C) between the indolin‐2‐one units. Intermolecular π–π stacking interactions are also observed. 相似文献
9.
Diana Becerra Braulio Insuasty Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2010,66(2):o79-o86
The molecules of racemic 3‐benzoylmethyl‐3‐hydroxyindolin‐2‐one, C16H13NO3, (I), are linked by a combination of N—H...O and O—H...O hydrogen bonds into a chain of centrosymmetric edge‐fused R22(10) and R44(12) rings. Five monosubstituted analogues of (I), namely racemic 3‐hydroxy‐3‐[(4‐methylbenzoyl)methyl]indolin‐2‐one, C17H15NO3, (II), racemic 3‐[(4‐fluorobenzoyl)methyl]‐3‐hydroxyindolin‐2‐one, C16H12FNO3, (III), racemic 3‐[(4‐chlorobenzoyl)methyl]‐3‐hydroxyindolin‐2‐one, C16H12ClNO3, (IV), racemic 3‐[(4‐bromobenzoyl)methyl]‐3‐hydroxyindolin‐2‐one, C16H12BrNO3, (V), and racemic 3‐hydroxy‐3‐[(4‐nitrobenzoyl)methyl]indolin‐2‐one, C16H12N2O5, (VI), are isomorphous in space group P. In each of compounds (II)–(VI), a combination of N—H...O and O—H...O hydrogen bonds generates a chain of centrosymmetric edge‐fused R22(8) and R22(10) rings, and these chains are linked into sheets by an aromatic π–π stacking interaction. No two of the structures of (II)–(VI) exhibit the same combination of weak hydrogen bonds of C—H...O and C—H...π(arene) types. The molecules of racemic 3‐hydroxy‐3‐(2‐thienylcarbonylmethyl)indolin‐2‐one, C14H11NO3S, (VII), form hydrogen‐bonded chains very similar to those in (II)–(VI), but here the sheet formation depends upon a weak π–π stacking interaction between thienyl rings. Comparisons are drawn between the crystal structures of compounds (I)–(VII) and those of some recently reported analogues having no aromatic group in the side chain. 相似文献
10.
11.
Heteroannulation of Arynes with α‐Amino Imides: Synthesis of 2,2‐Disubstituted Indolin‐3‐ones and Application to the Enantioselective Total Synthesis of (+)‐Hinckdentine A
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Dr. Rubén O. Torres‐Ochoa Dr. Thomas Buyck Dr. Qian Wang Prof. Dr. Jieping Zhu 《Angewandte Chemie (International ed. in English)》2018,57(20):5679-5683
A novel heteroannulation reaction between α‐amino imides and in situ generated arynes has been developed for the synthesis of 2,2‐disubstituted indolin‐3‐ones. An enantioselective total synthesis of the marine alkaloid (+)‐hinckdentine A was subsequently accomplished using this reaction as a key step. A catalytic enantioselective Michael addition of an α‐aryl‐α‐isocyanoacetate to phenyl vinyl selenone was employed for the construction of the enantioenriched α‐quaternary α‐amino ester. 相似文献
12.
Enantioselective Visible‐Light‐Induced Radical‐Addition Reactions to 3‐Alkylidene Indolin‐2‐ones
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Dr. Dominik Lenhart Dr. Andreas Bauer Dr. Alexander Pöthig Prof. Dr. Thorsten Bach 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(19):6519-6523
The title compounds underwent a facile and high‐yielding addition reaction (19 examples, 66–99 % yield) with various N‐(trimethylsilyl)methyl‐substituted amines upon irradiation with visible light and catalysis by a metal complex. If the alkylidene substituent is non‐symmetric and if the reaction is performed in the presence of a chiral hydrogen‐bonding template, products are obtained with significant enantioselectivity (58–72 % ee) as a mixture of diastereoisomers. Mechanistic studies suggest a closed catalytic cycle for the photoactive metal complex. However, the silyl transfer from the amine occurs not only to the product, but also to the substrate, and interferes with the desired chirality transfer. 相似文献
13.
An isatin‐based fluorophore, 3‐(pyrimidin‐2‐ylimino)indolin‐2‐one, was grafted on a large‐pore mesoporous silica material (SBA‐15) via a two‐step modification process. The obtained material (SBA‐Is‐Py) was characterized using various techniques and the characterization showed that the ordered porous structure was preserved after the post‐grafting procedure. The optical sensing ability of SBA‐Is‐Py was studied upon the addition of a variety of metal ions and a marked fluorescence quenching by Hg2+ ion was observed. SBA‐Is‐Py exhibited excellent Hg2+‐specific luminescence quenching over various competing cations. Furthermore, linear changes of the optical properties of SBA‐Is‐Py as a function of the concentrations of Hg2+ ion were found, with a calculated detection limit of 3.28 × 10?7 M. In addition, SBA‐Is‐Py was successfully employed for the determination of Hg2+ in real water samples. 相似文献
14.
Qing‐Xia Zhang Yao Li Jie Wang Chen Yang Cheng‐Jun Liu Xin Li Jin‐Pei Cheng 《Angewandte Chemie (International ed. in English)》2020,59(11):4550-4556
The enantioselective ketimine–ene reaction is one of the most challenging stereocontrolled reaction types in organic synthesis. In this work, catalytic enantioselective ketimine–ene reactions of 2‐aryl‐3H‐indol‐3‐ones with α‐methylstyrenes were achieved by utilizing a B(C6F5)3/chiral phosphoric acid (CPA) catalyst. These ketimine–ene reactions proceed well with low catalyst loading (B(C6F5)3/CPA=2 mol %/2 mol %) under mild conditions, providing rapid and facile access to a series of functionalized 2‐allyl‐indolin‐3‐ones with very good reactivity (up to 99 % yield) and excellent enantioselectivity (up to 99 % ee). Theoretical calculations reveal that enhancement of the acidity of the chiral phosphoric acid by B(C6F5)3 significantly reduces the activation free energy barrier. Furthermore, collective favorable hydrogen‐bonding interactions, especially the enhanced N?H???O hydrogen‐bonding interaction, differentiates the free energy of the transition states of CPA and B(C6F5)3/CPA, thereby inducing the improvement of stereoselectivity. 相似文献
15.
16.
A one‐pot four component condensation of isatin, sarcosine, 2‐[2‐oxo‐1‐(prop‐2‐ynyl)indolin‐3‐ylidene]malononitrile and aryl azides has been reported for the synthesis of novel dispirooxindole pyrrolidine linked 1,2,3‐triazole conjugates using Cu(I) as a catalyst in PEG‐400 by stereoselective [3 + 2] azide‐alkyne cycloaddition followed by [3 + 2] azomethine ylide and alkene cycloaddition. Structures have been confirmed by spectral and X‐ray studies. Crystal packing of 5a has also been reported. Rapid reaction, easy work‐up and high yields are the salient features of the present protocol. 相似文献
17.
Chepuri V. Suneel Kumar Dr. Vedavati G Puranik Dr. Chepuri V. Ramana 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(31):9601-9611
A strategy directed towards the total synthesis of isatisine A that involves several late‐stage metal‐catalyzed transformations that address the key carbon–carbon and carbon–heteroatom bond formations has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2‐disubstituted N‐hydroxyindolin‐3‐one or 2,2‐disubstituted indolin‐3‐one compounds have been developed by employing InCl3 as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate its viability, the synthesis of 13‐deoxy‐isatisine A has been completed in ten steps from a known and easily available lactone. 相似文献
18.
Moônica M. Bastos Lúcia M. U. Mayer Elza C. S. Figueira Marcio Soares Núbia Boechat Warner B. Kover 《Journal of heterocyclic chemistry》2008,45(4):969-973
19.
Sadif A. Shirvan Ramin Ghahremanzadeh Mojtaba Mirhosseini Moghaddam Ayoob Bazgir Amir Hassan Zarnani Mohammad Mehdi Akhondi 《Journal of heterocyclic chemistry》2012,49(4):951-954
Synthesis of spiro[indoline‐pyrazolo[4′,3′:5,6]pyrido[2,3‐d]pyrimidine]trione derivatives by a cyclo‐condensation reaction of indolin‐2‐ones, barbituric acids, and 1,3‐diphenyl‐1H‐pyrazol‐5‐amines with the ionic liquid as an effective green reaction media and in the presence of Alum as a reusable catalyst was reported. Excellent yields of products, green media, use of a reusable catalyst, and short reaction time are the main advantages of this new method. 相似文献
20.
An Efficient Synthesis of 3‐(3‐benzyl‐2‐(phenylimino)‐2,3‐dihydrothiazol‐4‐yl)‐6‐methyl‐4‐(2‐oxo‐2‐phenylethoxy)‐3,4‐dihydro‐2H‐pyran‐2‐one Derivatives via Multi‐Component Approach
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An easy, highly efficient and a new convenient one‐pot, two‐step approach to the synthesis of 3‐(3‐benzyl‐2‐(phenylimino)‐2,3‐dihydrothiazol‐4‐yl)‐6‐methyl‐4‐(2‐oxo‐2‐phenylethoxy)‐3,4‐dihydro‐2H‐pyran‐2‐one is described. These compounds were synthesized from 3‐(3‐benzyl‐2‐(phenylimino)‐2,3‐dihydrothiazol‐4‐yl)‐4‐hydroxy‐6‐methyl‐3,4‐dihydro‐2H‐pyran‐2‐one and α‐bromoketones in good yields. The compounds 4 were synthesized by a multi‐component reaction between 1 , 2 , and 3 and the prominent features of this protocol are mild reaction conditions, operation simplicity, and good to high yields of products. 相似文献