- An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds
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Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new, previously inaccessible vectors and used to access a novel analogue of ganaplacide.
- Bond, Andrew D.,Hanby, Abigail R.,King, Thomas A.,Moss, Thomas A.,Sore, Hannah F.,Spring, David R.,Stewart, Hannah L.
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supporting information
p. 6818 - 6821
(2020/07/04)
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- Synthesis of Highly Fused Pyrano[2,3- b]pyridines via Rh(III)-Catalyzed C-H Activation and Intramolecular Cascade Annulation under Room Temperature
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A facile access to the polycyclic-fused pyrano[2,3-b]pyridines has been established under room temperature via Rh(III)-catalyzed C-H bond activation and intramolecular cascade annulation. This strategy features high efficiency, unique versatility, and gen
- Han, Xu,Gao, Feng,Li, Chunpu,Fang, Daqing,Xie, Xiong,Zhou, Yu,Liu, Hong
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supporting information
p. 6281 - 6294
(2020/03/05)
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- Benzimidates as gem-Diamidation and Amidoindolyzation Cascade Synthons with a Hydrated NiII Catalyst
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We contributed a new benzimidate chemistry through moisture-insensitive NiII/NiII-FeIII combo-catalysis for a simultaneous 2-3 bond-forming gem-diamidation and amidoindolyzation cascade reaction to construct symmetrical an
- Nandi, Rajesh,Mandal, Prakash K.,Kayet, Anirban,Bhattachariya, Tamalika,Ghosh, Sukla,Maiti, Dilip K.
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supporting information
p. 3474 - 3478
(2020/04/20)
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- Rh(III)-Catalyzed [3 + 2] Annulation via C-H Activation: Direct Access to Trifluoromethyl-Substituted Indenamines and Aminoindanes
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The rhodium(III)-catalyzed direct C-H addition and annulation of benzimidates and aldimines with β-(trifluoromethyl)-α,β-unsaturated ketones is described. This protocol provides the facile and efficient formation of various trifluoromethyl-containing inde
- Chaudhary, Bharatkumar,Auti, Prashant,Shinde, Suchita Dattatray,Yakkala, Prasanna Anjaneyulu,Giri, Deepesh,Sharma, Satyasheel
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supporting information
p. 2763 - 2767
(2019/04/30)
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- Rhodium-Catalyzed Relay Carbenoid Functionalization of Aromatic C-H Bonds toward Fused Heteroarenes
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A rhodium-catalyzed annulation between ethyl benzimidates and α- aroyl sulfur ylides was developed, affording a series of pyrano[4,3,2-ij]isoquinoline derivatives in moderate to good yields with good functional group compatibility. The procedure featured
- Wu, Xiaopeng,Xiong, Hao,Sun, Song,Cheng, Jiang
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supporting information
p. 1396 - 1399
(2018/03/09)
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- Synthesis of Isoquinolines through IrIII-Catalyzed C–H Activation/Annulation from Benzimidates with Hydroxylisopropylalkynes
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An IrIII-catalyzed cascade reaction consisting of C–H activation/annulation of benzimidates with hydroxylisopropylalkynes is reported. A broad range of isoquinolines has been prepared in one step with good functiona-group tolerance and high eff
- Liu, Mingliang,Gong, Wanchun,You, Erli,Zhang, Haizhen,Shi, Lei,Cao, Weiguo,Shi, Jingjing
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supporting information
p. 4991 - 4995
(2018/10/05)
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- Controllable Rh(III)-Catalyzed C-H Arylation and Dealcoholization: Access to Biphenyl-2-carbonitriles and Biphenyl-2-carbimidates
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A controllable Rh(III)-catalyzed C-H arylation and dealcoholization of benzimidates with arylboronic esters was developed, delivering various biphenyl-2-carbonitriles and biphenyl-2-carbimidates by simply tuning the reaction conditions. This approach features high efficiency, good functional group tolerance, and easy operation. It also provides an alternative pathway to thoroughly exploit the directing group in transition-metal-catalyzed C-H activations.
- Jiang, Bo,Wu, Songxiao,Zeng, Jing,Yang, Xiaobo
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supporting information
p. 6573 - 6577
(2018/10/09)
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- Ruthenium (II)-Catalyzed Oxidant-Free Coupling/Cyclization of Benzimidates and Sulfoxonium Ylides to Form Substituted Isoquinolines
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A ruthenium-catalyzed direct mono-C?H functionalization/annulation cascade reaction of benzimidates and sulfoxonium ylides has been developed. The reaction proceeds smoothly with a broad range of substrates, giving access to a variety of isoquinoline deri
- Shi, Xinxia,Wang, Rongchao,Zeng, Xiaofei,Zhang, Yilan,Hu, Huiling,Xie, Chunsong,Wang, Min
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supporting information
p. 4049 - 4053
(2018/09/21)
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- Synthesis of Functionalized Indenones via Rh-Catalyzed C-H Activation Cascade Reaction
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An efficient and expeditious protocol for the synthesis of diverse difunctionalized indenones through rhodium-catalyzed C-H activation and multistep cascade reaction of benzimidates and alkenes has been developed. The transformation involves the cleavage and formation of multiple bonds in one pot under mild reaction conditions, and Mn(OAc)2 plays an important role in the reaction.
- Lv, Ningning,Chen, Zhengkai,Liu, Yue,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 2588 - 2591
(2017/05/24)
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- Cobalt-Catalyzed Oxidant-Free Spirocycle Synthesis by Liberation of Hydrogen
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The first example of oxidant-free cobalt-catalyzed synthesis of five-membered spirocycles is reported from benzimidates and maleimides utilizing nitrobenzene as promoter. In contrast to previously known cobalt-catalyzed oxidative C-H functionalization rea
- Lv, Ningning,Liu, Yue,Xiong, Chunhua,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 4640 - 4643
(2017/09/12)
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- Ruthenium(II)-Catalyzed Redox-Neutral Oxidative Cyclization of Benzimidates with Alkenes with Hydrogen Evolution
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1H-Isoindoles and 2H-isoindoles are synthesized via a ruthenium-catalyzed oxidant-free cyclization of benzimidates with alkenes at room temperature with the liberation of H2. Later, 1H-isoindoles were converted into nitrogen-containing heterocy
- Manikandan, Rajendran,Tamizmani, Masilamani,Jeganmohan, Masilamani
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supporting information
p. 6678 - 6681
(2017/12/26)
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- Synthesis of 1H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis
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Nitrosobenzenes have been used as a convenient aminating reagent for the efficient synthesis of 1H-indazoles via rhodium and copper catalyzed C-H activation and C-N/N-N coupling. The reaction occurred under redox-neutral conditions with high efficiency and functional group tolerance. Moreover, a rhodacyclic imidate complex has been identified as a key intermediate.
- Wang, Qiang,Li, Xingwei
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supporting information
p. 2102 - 2105
(2016/06/01)
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- Structure-activity relationship study to understand the estrogen receptor-dependent gene activation of aryl- and alkyl-substituted 1H-imidazoles
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A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE wtcluc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4- hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.
- Wiglenda, Thomas,Gust, Ronald
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p. 1475 - 1484
(2007/10/03)
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- A remarkably efficient Markovnikov hydrochlorination of olefins and transformation of nitriles into imidates by use of AcCl and an alcohol
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HCl generated by mixing AcCl with EtOH brings about Markovnikov hydrochlorination of olefins in excellent yields. The products are isolated in states of high purity simply by removal of the volatile components under reduced pressure. Further, nitriles are transformed into imidate hydrochlorides on similar treatment with AcCl and an alcohol. This procedure for nitrile-imidate transformation is much more efficient than that used previously, which involved continuous passing of HCl gas into the solution of a nitrile in a solvent such as Et2O or benzene and an alcohol until one equivalent had been absorbed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Yadav, Veejendra K.,Babu, K. Ganesh
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p. 452 - 456
(2007/10/03)
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- SYNTHESE ET REACTIVITE D'ARYL ET ALKYL-2 (4H) PYRIDO THIAZINE-1,3 ONES-4
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2-Aryl and alkyl pyrido -1,3-thiazine-4(4H)-ones, a class of previously unknown compounds can be conveniently prepared by treatment of the sodium anion of 2-chloronicotinamide with various aromatic and aliphatic thioesters.Their reduction with sodi
- Couture, Axel,Grandclaudn, Pierre,Huguerre, Eric
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p. 4153 - 4162
(2007/10/02)
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- A Facile and Concise Synthesis of 2-Alkyl- and 2-Aryl-4-oxo-4H-thiopyranopyridines
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2-Alkyl- and 2-aryl-4-oxo-4H-thiopyranopyridine can be conveniently prepared by reacting the appropriate aromatic and aliphatic O-ethyl thiocarboxylates with the sodium derivative of various alkyl 3-(2-bromopyridyl) ketones.
- Couture, Axel,Grandclaudon, Pierre,Huguerre, Eric
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p. 456 - 457
(2007/10/02)
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