- Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
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We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.
- Delcaillau, Tristan,Boehm, Philip,Morandi, Bill
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supporting information
p. 3723 - 3728
(2021/04/07)
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- Nickel-Catalyzed Cyanation of Aryl Thioethers
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A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.
- Delcaillau, Tristan,Woenckhaus-Alvarez, Adrian,Morandi, Bill
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supporting information
p. 7018 - 7022
(2021/09/13)
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- Design and synthesis of C3-symmetric molecules containing oxepine and benzofuran moieties via Metathesis
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We report a new synthetic strategy to C3-symmetric star-shaped phenyl and triazine central cores bearing oxepine and benzofuran ring systems. In this regard, we have explored the application of metathetic strategy to construct C3-sym
- Gupta, Naveen Kumar,Kotha, Sambasivarao,Solanke, Balaji. U.
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- Method for converting aromatic aldehyde into aromatic nitrile by using sulfur powder promoted inorganic ammonium as nitrogen source (by machine translation)
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The invention discloses a method for converting aromatic aldehyde into aromatic nitrile. The method is conversion of high yield of aromatic aldehyde one-pot reaction of sulfur powder promoted inorganic ammonium as a nitrogen source into aromatic nitrile. The method has the advantages of no need of metal participation, no need of strong oxide, compatibility of reaction to air, easiness in amplification to a gram scale and the like, and overcomes the problems of harsh reaction conditions, complex operation, low functional group compatibility and the like in the prior art. (by machine translation)
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Paragraph 0084; 0085
(2020/09/12)
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- Difluorocarbene-Based Cyanation of Aryl Iodides
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A large number of efficient cyanation methods have been developed because of the wide range of applications of nitriles, but conventional methods usually suffer from the need for a toxic cyanation reagent. Although difluorocarbene chemistry has received increasing attention, the use of difluorocarbene as a sources of the nitrile carbon for nitrile groups remains largely unexplored. We describe a difluorocarbene-based cyanation of aryl iodides promoted by a cheap copper source, Cu(NO 3) 2 ·2.5H 2 O, under an air atmosphere. Ph 3 P + CF 2 CO 2-, an easily available and shelf-stable difluorocarbene reagent, and NaNH 2 are used as the carbon source and the nitrogen source for the nitrile group, respectively. The cyanation protocol is attractive because no toxic reagent is used and performing the reactions under an air atmosphere is operationally convenient.
- Cao, Yu-Cai,Du, Ruo-Bing,Fu, Zhi-Hong,Guo, Yu,Lin, Jin-Hong,Xiao, Ji-Chang,Xiao, Xuan,Yao, Xu,Zhang, Yin-Xiang,Zheng, Xing
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supporting information
p. 713 - 717
(2020/04/08)
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- Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters
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The first example of intramolecular ring-opening and reconstruction of cyclobutanone oxime esters via selective C-C bond cleavage leading to the synthesis of 3,4-dihydronaphthalene-2-carbonitriles in the presence of a cheap copper catalyst has been reported. The protocol is distinguished by mild and safe reaction conditions that exclude ligands, oxidants, bases, toxic cyanide salts and tolerates a wide scope of cyclobutanones without compromising their efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.
- Wang, Panpan,Zhao, Binlin,Yuan, Yu,Shi, Zhuangzhi
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supporting information
p. 1971 - 1974
(2019/05/02)
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- Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor
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In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.
- Cai, Wenqing,Wu, Jingwei,Liu, Wei,Xie, Yafei,Liu, Yuqiang,Zhang, Shuo,Xu, Weiren,Tang, Lida,Wang, Jianwu,Zhao, Guilong
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- Identification of 4-(2-furanyl)pyrimidin-2-amines as Janus kinase 2 inhibitors
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Janus kinases inhibitor is considered to have therapeutic potential for the treatment of oncology and immune-inflammatory diseases. Two series of 4-(2-benzofuranyl)pyrimidin-2-amine and 4-(4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-yl)pyrimidin-2-amine derivatives have been designed and synthesized. Primary SAR studies resulted in the discovery of a novel class of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine based JAK2 inhibitors with higher potency (IC50of 0.7 nM) and selectivity (>30 fold) to JAK3 kinase than tofacitinib.
- Wang, Yazhou,Huang, Wei,Xin, Minhang,Chen, Pan,Gui, Li,Zhao, Xinge,Tang, Feng,Wang, Jia,Liu, Fei
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- NOVEL TRICYCLIC CALCIUM SENSING RECEPTOR ANTAGONISTS FOR THE TREATMENT OF OSTEOPOROSIS
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Novel tricyclic compounds of the formula (I): and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing osteoporosis and similar conditions. The compounds are effective as calcium sensing receptor antagonists. Pharmaceutical compositions and methods of treatment are also included.
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Page/Page column 92
(2015/07/07)
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- NOVEL TRICYCLIC CALCIUM SENSING RECEPTOR ANTAGONISTS
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Novel tricyclic compounds of Formula (I) and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing osteoporosis and similar conditions. The compounds are effective as calcium sensing receptor antagonists. Pharmaceutical compositions and methods of treatment are also included.
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Page/Page column 93
(2015/07/07)
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- One-pot synthesis of amidoxime via Pd-catalyzed cyanation and amidoximation
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A novel "one-pot" reaction was developed for the synthesis of aryl or heteroaryl-substituted amidoxime compounds containing various functional groups. Fluorescence titration experiments coupled with theoretical analysis revealed that the steric hindrance and electronic effects of substituents influence the binding ability of the amidoxime compounds to uranyl ions. This journal is
- Yang, Chu-Ting,Han, Jun,Liu, Jun,Gu, Mei,Li, Yi,Wen, Jun,Yu, Hai-Zhu,Hu, Sheng,Wang, Xiaolin
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supporting information
p. 2541 - 2545
(2015/04/14)
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- Cycloisomerization of aromatic homo and bis-homopropargylic alcohols via catalytic ru vinylidenes: Formation of benzofurans and isochromenes
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Ru-catalyzed cycloisomerizations of aromatic homo- and bis-homopropargylic alcohols effectively afford benzofurans and isochromenes. These processes proved to be chemo- and regioselective (5-, and 6-endo cyclizations) derived from key Ru vinylidene intermediates. The presence of an amine/ammonium base-acid pair is crucial for the catalytic cycle.
- Varela-Fernandez, Alejandro,Gonzalez-Rodriguez, Carlos,Varela, Jesus A.,Castedo, Luis,Saa, Carlos
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supporting information; experimental part
p. 5350 - 5353
(2009/12/30)
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- The synthesis and transition temperatures of 2-(4-alkyl- and 4-alkoxy-phenyl)-5-cyano-1-benzofurans and related diaryl-1-benzofurans - An assessment of how deviations from linearity and conformational effects in a core unit affect mesogenicity
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The synthesis and transition temperatures are reported for several 2-(4-alkyl- and 4-alkoxy-phenyl)-5-cyano-1-benzofurans, 2-(4′-alkylbiphenyl-4-yl)-5-cyano- and 5-(4′-alkylbiphenyl-4-yl)-2-cyano-1-benzofurans, and for compounds with other combinations of terminal alkyl and cyano groups in 2,5-disubstituted-1-benzofurans containing two phenyl units, some isolated examples of related cyclohexane systems are also presented. The mesogenic behaviour of these compounds and several intermediates (e.g. amides, acids and esters) is discussed and the transition temperatures are rationalised on the following basis (a) 1-benzofuran is a superior core unit to benzene, (b) 2,5-disubstitution in 1-benzofuran gives a bent core which adversely affects mesogenicity, to an extent which depends on its position in the core, (c) antiparallel associations in terminal cyano compounds can eliminate the disadvantage of a bent core structure, (d) 2-aryl-1-benzofurans have negligible inter-annular twist but 5-aryl-1-benzofurans have similar inter-annular twist to that in biphenyls.
- Friedman,Toyne,Goodby,Hird
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p. 2759 - 2772
(2007/10/03)
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- Heterobicyclic keto- and amino-acids, esters and amides
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Heterobicyclic glyoxylic acids, L- and DL-heterobicyclic glycines and their derivatives of the formulae STR1 and pharmaceutically acceptable cationic and acid addition salts thereof, wherein R is OR2 or NHR3 ; R2 is hydrogen or alkyl having from one to four carbon atoms; R3 is hydrogen, alkyl having from one to four carbon atoms, alkoxyalkyl having from one to four carbon atoms in each of the alkyl groups or R4 R5 C6 H3 CH2 -- where R4 and R5 are H, OH, F, Cl, Br, I, or alkyl or alkoxy having from one to four carbon atoms R1 is hydrogen, alkyl having from one to four carbon atoms or R4 R5 C6 H3 --; X is oxygen or sulfur; n is 0 or 1 and the broken line represents an optionally present double bond; useful in treatment of diseases and conditions which are characterized by reduced blood flow, reduced oxygen availability or reduced carbohydrate metabolism in the cardiovascular system.
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