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1.
《化学:亚洲杂志》2017,12(7):734-743
A transition‐metal (TM)‐free and halogen‐free NaOt Bu‐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. 相似文献
2.
FeIII‐Catalyzed Cross‐Dehydrogenative Arylation (CDA) between Oxindoles and Arenes under an Air Atmosphere 下载免费PDF全文
Hong‐Ru Wu Hong‐Yan Huang Dr. Chuan‐Li Ren Prof. Dr. Li Liu Prof. Dong Wang Prof. Dr. Chao‐Jun Li 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(47):16744-16748
An efficient FeIII‐catalyzed cross‐dehydrogenative arylation (CDA) of 3‐substituted oxindoles with activated arenes under an air atmosphere was developed to provide 3,3′‐disubstituted oxindoles in good yields. 相似文献
3.
Li L Chen W Yang W Pan Y Liu H Tan CH Jiang Z 《Chemical communications (Cambridge, England)》2012,48(42):5124-5126
A bicyclic guanidine-catalyzed Michael addition of 3-benzyl substituted oxindoles to N-maleimides has been developed to produce oxindole derivatives with a quaternary carbon chiral center at the 3-position in excellent yields and enantio- and diastereoselectivities. This is the first incorporation of N-benzylic α-branched succinimides into 3,3-disubstituted oxindoles. 相似文献
4.
Organocatalytic Highly Enantioselective Substitution of 3‐(1‐Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)‐Trigolutes B 下载免费PDF全文
Jian‐Zhou Huang Chen‐Long Zhang Yi‐Fan Zhu Lu‐Lu Li Dian‐Feng Chen Zhi‐Yong Han Prof. Dr. Liu‐Zhu Gong 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(23):8389-8393
A highly enantioselective organocatalytic substitution of 3‐(1‐tosylalkyl)indoles with oxindoles has been established by using chiral bifunctional organocatalysts, providing an efficient entry to multiply functionalized 3,3′‐disubstituted oxindoles, and was exploited as the key step to enable the first asymmetric total synthesis of optically pure (+)‐trigolutes B to be accomplished in a concise manner, within seven steps with an 18 % overall yield. 相似文献
5.
This paper presents a synthetically challenging vicinal quaternary-tertiary C–C forming reaction of 3-substituted oxindoles and chalcones by a simple aryl substituted bifunctional thiourea catalyst. The reactions work with a broad range of chalcones, giving chiral 3,3′-substituted oxindoles type compounds with adjacent quaternary-tertiary stereocenters in high yields (up to 99%), very good dr (up to >98:2) and very good ee (up to 96%). 相似文献
6.
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
7.
8.
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
9.
Zhao-Min Liu Nai-Kai LiXiao-Fei Huang Bing WuNing Li Chun-Yuen KwokYong Wang Xing-Wang Wang 《Tetrahedron》2014
The enantioselective Michael addition of dialkyl phosphites to N-unprotected isatylidene malononitriles has been established for the first time by using a simple bifunctional tertiary amine–thiourea catalyst. The corresponding adducts, 3-phospho-2-oxindoles, containing a chiral quaternary carbon center at the 3-position of the oxindole, were obtained in good to excellent yields (up to 98%) with moderate to excellent enantioselectivities (up to 95% ee). In addition, optically active 3,3′-disubstituted oxindoles bearing carboxylate and phosphonate groups were facilely obtained by the oxidative degradation of the Michael adducts. 相似文献
10.
《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(50):16161-16165
The active complexes of chiral N,N′‐dioxide ligands with dysprosium and magnesium salts catalyze the hetero‐Diels–Alder reaction between 2‐aza‐3‐silyloxy‐butadienes and alkylidene oxindoles to selectively form 3,3′‐ and 3,4′‐piperidinoyl spirooxindoles, respectively, in very high yields and with excellent enantioselectivities. The exo ‐selective asymmetric cycloaddition successfully regaled the construction of sp3‐rich and highly substituted natural‐product‐based spirooxindoles supporting many chiral centers, including contiguous all‐carbon quaternary centers. 相似文献
11.
本课题组近年来发展的通过路易斯碱催化靛红Morita-Baylis-Hillman(MBH)碳酸酯的烯丙基烷基化反应是合成光学纯3,3-二取代2-氧化吲哚化合物的一种有效方法. 在此基础上, 本文研究了手性叔胺催化靛红MBH碳酸酯与环状N-磺酰亚胺的不对称烯丙基烷基化反应, 通过亲电反应途径以较高的立体选择性(达86% ee, dr>95∶5)和高收率(达96%)合成C-3位含季碳手性中心的多官能团氧化吲哚产物. 通过简单的转化可以得到含多个手性中心的2-吲哚酮-3,4'-哌啶环类骨架, 这为进一步合成生理活性物质研究奠定了基础. 相似文献
12.
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
13.
《Journal of heterocyclic chemistry》2017,54(1):147-150
Aldol condensation of 5,6‐dihydro‐4H‐pyrrolo[3,2,1‐ij ]quinoline‐1,2‐dione with aryl methyl ketones generates 3‐(aroylmethylidene)oxindoles, which react with hydrazine to generate tricyclic spiro[3H‐pyrazole‐3,3′‐oxindoles]. 相似文献
14.
Dr. Jean‐Nicolas Desrosiers Liana Hie Dr. Soumik Biswas Dr. Olga V. Zatolochnaya Dr. Sonia Rodriguez Dr. Heewon Lee Dr. Nelu Grinberg Dr. Nizar Haddad Dr. Nathan K. Yee Prof. Neil K. Garg Dr. Chris H. Senanayake 《Angewandte Chemie (International ed. in English)》2016,55(39):11921-11924
A nickel‐catalyzed Heck cyclization for the construction of quaternary stereocenters is reported. This transformation is demonstrated in the synthesis of 3,3‐disubstituted oxindoles, which are prevalent motifs seen in numerous biologically active molecules. The method shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct stereochemically complex frameworks by nonprecious‐metal catalysis. 相似文献
15.
Xingfeng Bai Caizhi Wu Shaozhong Ge Yixin Lu 《Angewandte Chemie (International ed. in English)》2020,59(7):2764-2768
An asymmetric palladium and copper co‐catalyzed Heck/Sonogashira reaction between o‐iodoacrylanilides and terminal alkynes to synthesize chiral oxindoles was developed. In particular, a wide range of CF3‐substituted o‐iodoacrylanilides reacted with terminal alkynes, affording the corresponding chiral oxindoles containing trifluoromethylated quaternary stereogenic centers in high yields with excellent enantioselectivities (94–98 % ee). This asymmetric Heck/Sonogashira reaction provides a general approach to access oxindole derivatives containing quaternary stereogenic centers including CF3‐substituted ones. 相似文献
16.
Dr. Dmitry Katayev Prof. Yi‐Xia Jia Akhilesh K. Sharma Dr. Dipshikha Banerjee Dr. Céline Besnard Prof. Raghavan B. Sunoj Prof. E. Peter Kündig 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(36):11916-11927
Palladium complexes incorporating chiral N‐heterocyclic carbene (NHC) ligands catalyze the asymmetric intramolecular α‐arylation of amides producing 3,3‐disubstituted oxindoles. Comprehensive DFT studies have been performed to gain insight into the mechanism of this transformation. Oxidative addition is shown to be rate‐determining and reductive elimination to be enantioselectivity‐determining. The synthesis of seven new NHC ligands is detailed and their performance is compared. One of them, L8 , containing a tBu and a 1‐naphthyl group at the stereogenic centre, proved superior and was very efficient in the asymmetric synthesis of fifteen new spiro‐oxindoles and three azaspiro‐oxindoles often in high yields (up to 99 %) and enantioselectivities (up to 97 % ee; ee=enantiomeric excess). Three palladacycle intermediates resulting from the oxidative addition of [Pd(NHC)] into the aryl halide bond were isolated and structurally characterized (X‐ray). Using these intermediates as catalysts showed alkene additives to play an important role in increasing turnover number and frequency. 相似文献
17.
《Journal of heterocyclic chemistry》2017,54(2):944-951
Reaction of 5,6‐dihydro‐4H‐pyrrolo[3,2,1‐ij ]quinoline‐1,2‐dione ( 3 ) with two equivalents of cyclic 1,3‐dicarbonyl compounds under acid catalysis generates spiro[4H‐pyran‐3,3′‐oxindoles] 7 . In contrast, though base catalysis also achieves double addition, the final products 8 result from subsequent ring opening of the five‐membered lactam via intramolecular attack by enolate; these products can be converted into the spiro[4H‐pyran‐3,3′‐oxindoles] by treatment with acid. 相似文献
18.
《Journal of heterocyclic chemistry》2018,55(1):226-239
Knoevenagel condensation of 5,6‐dihydro‐4H‐pyrrolo[3,2,1‐ij]quinoline‐1,2‐dione 3 with aryl cyanomethyl ketones 9 generates 3‐(aroyl(cyano)methylidene)oxindoles 10 that react with cyclic 1,3‐diketones 11 to generate polycyclic hemiacetal spiro[4H‐2,3‐dihydropyran‐3,3′‐oxindoles] 13 . 相似文献
19.
By employing a chiral bifunctional thiourea-tertiary amine as catalyst, enantioselective tandem Michael addition-oxidation of 3-monosubstituted oxindoles with 1,4-benzoquinones were realized. The reactions afforded a wide range of 3,3-disubstituted oxindoles with moderate to good yields (up to 87%) in moderate to good enantioselectivities (up to 96%). 相似文献
20.
Microwave‐Assisted Copper‐Catalyzed Oxidative Cyclization of Acrylamides with Non‐Activated Ketones 下载免费PDF全文
Yaping Zhao Dr. Nandini Sharma Dr. Upendra K. Sharma Zhenghua Li Prof. Dr. Gonghua Song Prof. Dr. Erik V. Van der Eycken 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(17):5878-5882
An operationally simple and efficient microwave‐assisted protocol for the oxidative cyclization of acrylamide derivatives with non‐activated ketones to generate 3,3‐disubstituted oxindoles is described. The reaction proceeds by a copper‐catalyzed tandem radical addition/cyclization strategy and tolerates a series of functional groups with moderate to excellent yields. 相似文献