- Preparation and ring transformation of isomeric β-lactam derivatives of bicyclic 1,3-thiazines
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Ketene-imine cycloaddition reactions between cis- and trans-2-aryl-4a,5,6, 7,8,8a-hexahydro-4H-3,1-benzothazines and chloroacetyl chloride in the presence of base were investigated. Because of the diastereotopic CN faces of cyclohexane-condensed thiazines
- Fodor, Lajos,Csomós, Péter,Fül?p, Ferenc,Csámpai, Antal,Sohár, Pál
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Read Online
- Synthesis method of cyanoacrylate compound
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The method comprises the following reaction steps: a compound (1) reacts with a compound (2) to directly prepare a compound (3), and is characterized in that the reaction is carried out in a molten state. Compound (1). Compound (2). Compound (3).
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Paragraph 0022
(2021/09/21)
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- Understanding Mechanochromic Luminescence on Account of Molecular Level Based on Phosphorescent Iridium(III) Complex Isomers
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Mechanochromic luminescent (MCL) materials are promising in pressure sensors, security papers, photoelectric devices and optical data recording. Although some kinds of MCL-active iridium(III) complexes with various soft substituent functional ligands (e.g
- Li, Guangfu,Yang, Tianzhi,Shao, Kuizhan,Gao, Ying,Shan, Guogang,Su, Zhongmin,Wang, Xinlong,Zhu, Dongxia
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p. 3741 - 3748
(2021/04/07)
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- Sequential C-H activation enabled expedient delivery of polyfunctional arenes
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Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
- Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
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supporting information
p. 8075 - 8078
(2021/08/20)
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- 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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- Directed β C-H Amination of Alcohols via Radical Relay Chaperones
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A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.
- Wappes, Ethan A.,Nakafuku, Kohki M.,Nagib, David A.
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supporting information
p. 10204 - 10207
(2017/08/10)
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- The imine of the benzoate ester preparation method of the compound
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The invention discloses a benzimidate compound preparation method. According to the invention, a benzonitrile derivative represented by a formula (III) is subjected to a reaction with alcohol and a catalyst under a temperature of -30 DEG C to 50 DEG C, su
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Paragraph 0056; 0057; 0062; 0063; 0064; 0065; 0066-0068
(2017/06/23)
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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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- Benzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate
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Carboxamide pyrazinyloxy benzoxaboroles were investigated with the goal to identify a molecule with satisfactory antimalarial activity, physicochemical properties, pharmacokinetic profile, in vivo efficacy, and safety profile. This optimization effort discovered 46, which met our target candidate profile. Compound 46 had excellent activity against cultured Plasmodium falciparum, and in vivo against P. falciparum and P. berghei in infected mice. It exhibited good PK properties in mice, rats, and dogs. It was highly active against the other 11 P. falciparum strains, which are mostly resistant to chloroquine and pyrimethamine. The rapid parasite in vitro reduction and in vivo parasite clearance profile of 46 were similar to those of artemisinin and chloroquine, two rapid-acting antimalarials. It was nongenotoxic in an Ames assay, an in vitro micronucleus assay, and an in vivo rat micronucleus assay when dosed orally up to 2000 mg/kg. The combined properties of this novel benzoxaborole support its progression to preclinical development.
- Zhang, Yong-Kang,Plattner, Jacob J.,Easom, Eric E.,Jacobs, Robert T.,Guo, Denghui,Freund, Yvonne R.,Berry, Pamela,Ciaravino, Vic,Erve, John C. L.,Rosenthal, Philip J.,Campo, Brice,Gamo, Francisco-Javier,Sanz, Laura M.,Cao, Jianxin
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p. 5889 - 5908
(2017/07/22)
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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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- A multi-substituted imidazole derivatives method for the preparation of
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The invention provides a preparation method of multifunctional group-substituted imidazole derivatives including derivatives of 2,4,5-trisubstituted imidazole and 2-amino-4,5-disubstituted imidazole, and the derivatives are generated by alkenyl nitrine de
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Paragraph 0029; 0030
(2017/04/11)
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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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- Rh(III)-Catalyzed C-C/C-N Coupling of Imidates with α-Diazo Imidamide: Synthesis of Isoquinoline-Fused Indoles
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Imidate esters and diazo compounds have been established as bifunctional substrates for the construction of biologically active fused heterocycles via rhodium-catalyzed C-H activation and C-C/C-N coupling. This reaction occurs under mild conditions with high efficiency, step economy, and low catalyst loading.
- Wang, He,Li, Lei,Yu, Songjie,Li, Yunyun,Li, Xingwei
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supporting information
p. 2914 - 2917
(2016/07/06)
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- Manganese-Catalyzed ortho-C?H Alkenylation of Aromatic N?H Imidates with Alkynes: Versatile Access to Mono-Alkenylated Aromatic Nitriles
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So far, the direct C?H alkenylation of aromatic nitriles with alkynes has not been achieved. Herein, we discribe the first manganese-catalyzed C?H alkenylation of aromatic N?H imidates to access mono-alkenylated aromatic nitriles. The reaction is accelerated by the presence of a catalytic amount of sodium pivalate. This protocol is also highlighted by the simple catalytic system, good compatibility of functional groups, and excellent mono-/dialkenylation selectivity as well as E/Z stereoselectivity. (Figure presented.).
- Yang, Xiaoxu,Jin, Xiqing,Wang, Congyang
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p. 2436 - 2442
(2016/08/16)
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- C-H activation guided by aromatic N-H ketimines: Synthesis of functionalized isoquinolines using benzyl azides and alkynes
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Aromatic N-H ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic N-H ketimines, our protocol works under mild and neutral conditions, which enabled the synthesis of isoquinolines having various functionalities such as carbonyl, ester, alkenyl, and ether groups. In addition, the imidates generated from α-azido ethers were successfully used for the synthesis of 1-alkoxyisoquinolines.
- Gupta, Sreya,Han, Junghoon,Kim, Yongjin,Lee, Soon W.,Rhee, Young Ho,Park, Jaiwook
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p. 9094 - 9103
(2014/12/11)
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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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- IMMUNOMODULATORY COMPOUNDS AND METHODS OF USE THEREOF
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The present invention is directed to methods of treating diseases and disorders related to immune responses by administering one or more immunomodulatory compounds. In particular, the invention is directed to methods of stimulating and reducing immune responses, treating autoimmune conditions, treating allergic reactions and asthma, and preventing ischemic damage and asthma by administering one or more immunomodulatory compounds.
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- Radical azidonation of benzylic positions with iodoninm azide
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Introduction of an azido substituent at the α position of benzyl ethers can be achieved by treating them with IN3 in refluxing acetonitrile. Some of the products obtained after 20 min - 5 h are given.
- Viuf, Christel,Bols, Mikael
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p. 623 - 625
(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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- Synthesis and Structure of Alkyl N-Acylimidates
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Alkyl N-acylimidates 1 are prepared more easily and in higher yields than before by reaction of alkyl imidate hydrochlorides 5 with acyl halides 7 in the presence of 2.2 mol of base (14 examples).The X-ray analysis of a crystalline derivative (1dbd) shows, that the C=N- and C=O parts are twisted significantly (torsional angle 77.6 deg).The stereochemical, dynamic and electronic properties of the compounds 1 are interpreted by means of ab initio 3-21 G calculations on conformers of the parent system HO-CH=N-CH=O (8).Low rotational (ca. 6 kcal/mol) and inversional (max. 8 kcal/mol) barriers indicate the many favourable electronic interactions between the C=N- and the C=O groups in such N-functionalised imine derivatives.The compound 1 are significantly higher in energy than bisacylamines and are therefore suggested to be superior, more reactive synthetic C-N-C building blocks.The spectroscopic properties (IR, 13C- and 1H NMR, MS) are given and discussed.
- Kupfer, Rainer,Nagel, Michael,Wuerthwein, Ernst-Ulrich,Allmann, Rudolf
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p. 3089 - 3104
(2007/10/02)
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