- One-Step Synthesis of ortho-Hydroxycinnamaldehyde
-
An improved and convenient one-step procedure for the large scale synthesis of ortho-hydroxycinnamaldehyde (3a) using ortho-hydroxybenzaldehyde and vinyl acetate is described.
- Kim, Jong Han,Lee, Sangku,Kwon, Mu-Gil,Park, Yong Soo,Choi, Sung-Kyu,Kwon, Byoung-Mog
-
-
Read Online
- Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion
-
Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.
- Hayashi, Yujiro,Koshino, Seitaro,Kwon, Eunsang,Monde, Kenji,Taniguchi, Tohru
-
p. 15786 - 15794
(2021/10/14)
-
- Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand
-
The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.
- Zhao, Jiangui,Zheng, Xueli,Tao, Shaokun,Zhu, Yuxin,Yi, Jiwei,Tang, Songbai,Li, Ruixiang,Chen, Hua,Fu, Haiyan,Yuan, Maolin
-
supporting information
p. 6067 - 6072
(2021/08/16)
-
- Substrate-Controlled Chemo-/Enantioselective Synthesis of α-Benzylated Enals and Chiral Cyclopropane-Fused 2-Chromanone Derivatives
-
Substrate-controlled cascade reactions between α,β-unsaturated aldehydes or their analogues and 2,4-dinitrobenzyl chloride in the presence of a chiral secondary amine as the catalyst and base were developed, to obtain a broad spectrum of α-benzylated enals and enantioenriched cyclopropane-fused chroman-2-one derivatives. The cyclopropane-tethered iminium ion clearly served as a key intermediate in these reactions to trigger stereochemical outcomes, one of which was supported by a control experiment. (Figure presented.).
- Byeon, Huimyoung,Ryu, Sunghyeon,Yoo, Eun Jeong,Yang, Jung Woon
-
supporting information
p. 5085 - 5091
(2021/09/20)
-
- Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics
-
Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.
- Buijs, Ned,Campagna, Roberto,Emanuelli, Monica,Gao, Yongzhi,Innocenti, Paolo,Jespers, Willem,Martin, Nathaniel I.,Parsons, Richard B.,Sartini, Davide,Van Haren, Matthijs J.,Van Westen, Gerard J. P.,Zhang, Yurui,Gutiérrez-De-Terán, Hugo
-
p. 12938 - 12963
(2021/09/11)
-
- Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes
-
A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.
- Chen, Yuehua,Deng, Hao,Gao, Xing,Guo, Hongchao,Jiang, Feng,Wang, Wei,Wu, Yongjun,Zhu, Dongyu
-
supporting information
p. 7158 - 7163
(2020/10/02)
-
- Phosphorous acid promoted isomerization of propargyl alcohols to α,β-unsaturated carbonyl compounds
-
A metal-free and two-phase protocol for the Meyer-Schuster isomerization of propargyl alcohols to the corresponding α,β-unsaturated carbonyl compounds has been achieved in the presence of stoichiometric phosphorous acid aqueous solution, which produces the desired products in high yields with excellent stereoselectivity. Compared with the traditional methods, the procedure features broad scope of the substrates, mild conditions, and easy separation, providing an appealing alternative to the Meyer-Schuster reaction.
- Gan, Xiaotang,Fu, Zuqi,Liu,Yan, Yani,Chen, Chao,Zhou, Yongbo,Dong, Jianyu
-
-
- Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes
-
A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.
- Bhowmik, Amit,Fernandes, Rodney A.
-
supporting information
p. 9203 - 9207
(2019/11/14)
-
- PHARMACEUTICAL COMPOUNDS
-
The invention provides compounds of the formula (1) or salts or tautomers thereof; wherein: Q is SO or SO2; n is 1 or 2; R1 is selected from hydrogen and a non-aromatic C1-6 hydrocarbon group; R2 and R3 are independently selected from hydrogen and a C1-6 hydrocarbon group; or R2 and R3 together with the carbon atom to which they are attached form a carbonyl group (C=O), a cyclopropane-1,1-diyl group or a cyclobutane-1,1-diyl group; or R together with R2 forms a C2-4 alkylene linker which is optionally substituted with one or more substituents selected from a C1-4 hydrocarbon group, halogen, hydroxy and amino; R4 and R5 are independently selected from hydrogen and a non-aromatic C1-6 hydrocarbon group; or R4 and R5 together with the carbon atom to which they are attached form a cyclopropane-1,1-diyl group or a cyclobutane-1,1-diyl group; and Ar1 is selected from phenyl, thiophenyl and furanyl,each being optionally substituted. The compounds are useful in medicine, for example in the treatment of diseases, such as cancers.
- -
-
Page/Page column 51
(2019/10/19)
-
- Palladium-catalyzed hydroformylation of terminal arylacetylenes with glyoxylic acid
-
A simple, practical and governable palladium-catalyzed hydroformylation of terminal arylacetylenes has been disclosed. The reaction proceeds under syngas-free conditions, using readily available glyoxylic acid as the formyl source, under mild conditions, giving rise to a broad range of α,β-unsaturated aldehydes.
- Liu, Yang,Cai, Liangzhen,Xu, Sheng,Pu, Weiwen,Tao, Xiaochun
-
supporting information
p. 2166 - 2168
(2018/03/06)
-
- Discovery of novel piperonyl derivatives as diapophytoene desaturase inhibitors for the treatment of methicillin-, vancomycin- and linezolid-resistant Staphylococcus aureus infections
-
Inhibition of S. aureus diapophytoene desaturase (CrtN) could serve as an alternative approach for addressing the tricky antibiotic resistance by blocking the biosynthesis of carotenoid pigment which shields the bacterium from host oxidant killing. In this study, we designed and synthesized 44 derivatives with piperonyl scaffold targeting CrtN and the structure-activity relationships (SARs) were examined extensively to bring out the discovery of 21b with potent efficacy and better hERG safety profile compared to the first class CrtN inhibitor benzocycloalkane derivative 2. Except the excellent pigment inhibitory activity against wild-type S. aureus, 21b also showed excellent pigment inhibition against four pigmented MRSA strains. In addition, H2O2 killing and human whole blood killing assays proved 21b could sensitize S. aureus to be killed under oxidative stress conditions. Notably, the murine study in vivo validated the efficacy of 21b against pigmented S. aureus Newman, vancomycin-intermediate S. aureus Mu50 and linezolid-resistant S. aureus NRS271.
- Wei, Hanwen,Mao, Fei,Ni, Shuaishuai,Chen, Feifei,Li, Baoli,Qiu, Xiaoxia,Hu, Linghao,Wang, Manjiong,Zheng, Xinyu,Zhu, Jin,Lan, Lefu,Li, Jian
-
p. 235 - 251
(2018/01/17)
-
- Synthesis of Aldehydes by Organocatalytic Formylation Reactions of Boronic Acids with Glyoxylic Acid
-
Reported herein is a conceptually novel organocatalytic strategy for the formylation of boronic acids. New reactivity is engineered into the α-amino-acid-forming Petasis reaction occurring between aryl boronic acids, amines, and glyoxylic acids to prepare aldehydes. The operational simplicity of the process and its ability to generate structurally diverse and valued aryl, heteroaryl, and α,β-unsaturated aldehydes containing a wide array of functional groups, demonstrates the practical utility of the new synthetic strategy.
- Huang, He,Yu, Chenguang,Li, Xiangmin,Zhang, Yongqiang,Zhang, Yueteng,Chen, Xiaobei,Mariano, Patrick S.,Xie, Hexin,Wang, Wei
-
supporting information
p. 8201 - 8205
(2017/06/30)
-
- Direct oxidative conversion of 3-aryl propionaldehydes to 3-aryl acroleins promoted by SOMO catalysis
-
A new direct oxidative transformation of 3-aryl propionaldehydes to 3-aryl acroleins promoted by SOMO catalysis has been realized with high efficiency under mild reaction conditions.
- Zhu, Jin,Yu, Shunting,Lu, Wenchao,Deng, Jing,Li, Jian,Wang, Wei
-
scheme or table
p. 1207 - 1209
(2012/03/26)
-
- Synthesis of 1,3,5-trisubstituted pyrazolines via Zn(ii)-catalyzed double hydroamination of enynes with aryl hydrazines
-
An efficient Zn(ii)-catalyzed intermolecular double hydroamination of 1,3-enynes with aryl hydrazines, for the synthesis of pyrazolines, has been discussed.
- Patil, Nitin T.,Singh, Vipender
-
p. 11116 - 11118
(2011/11/29)
-
- Transition metal-catalyzed synthesis of pyrroles from dienyl azides
-
(Chemical Equation Presented) A range of 2,5-disubstituted and 2,4,5-trisubstituted pyrroles can be synthesized from dienyl azides at room temperature using catalytic amounts of Znl2 or Rh2(O 2CC3F7)4.
- Dong, Huijun,Shen, Meihua,Redford, Joanne E.,Stokes, Benjamin J.,Pumphrey, Ashley L.,Driver, Tom G.
-
p. 5191 - 5194
(2008/09/17)
-
- Inhibition of chitin synthases and antifungal activities by 2′-benzoyloxycinnamaldehyde from Pleuropterus ciliinervis and its derivatives
-
In the course of search for potent chitin synthase inhibitors from natural resources, a novel chitin synthases inhibitor, 2′-benzoyloxycinnamaldehyde (2′-BCA) (I), was isolated from the aerial parts of Pleuropterus ciliinervis NAKAI. 2′-BCA inhibited chit
- Kang, Tae Hoon,Hwang, Eui Il,Yun, Bong Sik,Park, Ki Duk,Kwon, Byoung Mog,Shin, Chul Soo,Kim, Sung Uk
-
p. 598 - 602
(2008/02/02)
-
- Preparation of optically pure (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates by Candida parapsilosis ATCC 7330 mediated deracemisation of the racemates
-
Biocatalytic deracemisation of a range of racemic (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates using Candida parapsilosis ATCC 7330 resulted in pure (S)-enantiomers in yields of up to 80% and ee>99%.
- Thangavel, Vaijayanthi,Chadha, Anju
-
p. 4126 - 4133
(2007/10/03)
-
- Cinnamaldehydes inhibit cyclin dependent kinase 4/cyclin D1
-
A series of cinnamaldehydes was synthesized for the study of inhibitory activity against cyclin dependent kinases (CDKs). A couple of compounds selectively inhibited cyclin D1-CDK4 with an IC50 value of 7-18 μM. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Jeong, Ha-Won,Kim, Mi-Ran,Son, Kwang-Hee,Young Han, Mi,Ha, Ji-Hong,Garnier, Matthieu,Meijer, Laurent,Kwon, Byoung-Mog
-
p. 1819 - 1822
(2007/10/03)
-
- Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes
-
Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials.
- Daubresse, Nicolas,Francesch, Charlette,Rolando, Christian
-
p. 10761 - 10770
(2007/10/03)
-
- "Vinylogs" and "acetylenylogs" of β-adrenergic agents
-
Vinylogous (Groups III and V) and acetylenologous (Group IV) analogs of the classical β-adrenergic agents - stimulants and blockers - were prepared in order to evaluate the effect of degree of saturation, position of unsaturation and rigidity of the chain
- Nudelman, Abraham,Binnes, Yitschak,Shmueli-Broide, Naomi,Odessa, Yael,Hieble, J. Paul,Sulpizio, Anthony C.
-
p. 125 - 132
(2007/10/03)
-
- THE OXIDATION OF ALDEHYDES TO ACIDS WITH CALCIUM HYPOCHLORITE
-
Calcium hypochlorite is an efficient reagent for the oxidation of aldehydes to the corresponding acids.Reactions are carried out at ambient temperature in aqueous acetonitrile-acetic acid solution.Aliphatic aldehydes and aromatic aldehydes with electron withdrawing groups afford good to excellent yields.Nuclear chlorination is the preferred reaction in aromatic aldehydes with electron donating groups.
- Nwaukwa, Stephen O.,Keehn, Philip M.
-
p. 3131 - 3134
(2007/10/02)
-