cas 3179-09-7, 1-Methoxy-3-(2-nitrovinyl)benzene

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Triarylimidazo[1,2-a]pyridine-8-carbonitriles: solvent-free synthesis and their anti-cancer evaluation
In this study, we have presented the synthesis of novel 2,5,7-triarylimidazo[1,2-a]pyridine-8-carbonitriles from 2-amino-4,6-diarlypyridine-3-carbonitrile and nitrostyrene using FeCl3 (20 mol%) as Lewis acid under solvent-free conditions. A library of compounds with diverse substitutions have also been synthesized and screened for in-vitro anti-cancer activity against various cell lines such as A549 (Lung), HCT-116 (Colon), SW-620 (Colon), and MIAPACA (Pancreas).
Gupta, Annah,Sasan, Sonakshi,Kour, Avneet,Nelofar, Nargis,Manikrao Mondhe, Dilip,Kapoor, Kamal K.
p. 1813 - 1822
(2019)
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Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"
We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.
Gao, Fengyun,Guo, Yifei,Sun, Mengmeng,Wang, Yalan,Yang, Changyan,Wang, Yuqiang,Wang, Kairong,Yan, Wenjin
supporting information
p. 2584 - 2589
(2021/04/13)

Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase
Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.
Chen, Haifeng,Guo, Yanrong,Han, Xinya,Hu, Wei,Huang, Yunyuan,Ren, Yanliang,Tang, Zilong,Wang, Qi,Wei, Lin,Xia, Qinfei,Yan, Jufen
supporting information

(2020/07/23)

Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis
A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.
Chahal, Mandeep K.,Payne, Daniel T.,Matsushita, Yoshitaka,Labuta, Jan,Ariga, Katsuhiko,Hill, Jonathan P.
supporting information
p. 82 - 90
(2020/01/02)

NCC Pincer Ni (II) Complexes Catalyzed Hydrophosphination of Nitroalkenes with Diphenylphosphine
An efficient NCC pincer Ni (II)-catalyzed hydrophosphination of nitroalkenes with diphenylphosphine has been developed. Under the optimized conditions, both (hetero)aromatic and aliphatic nitroalkenes were well tolerated, irrespective of electronic effect, to provide the corresponding products in up to 99% yield.
Yan, Jing,Wang, Yan-Bing,Hou, Senyao,Shi, Linlin,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
(2020/08/21)

Co-Polymeric Nanosponges from Cellulose Biomass as Heterogeneous Catalysts for amine-catalyzed Organic Reactions
Heterogeneous catalysts prepared from biomass waste sources are attracting increasing interest. The reasons rely on the possibility of combining the virtuous approach of circular economy with the consolidated advantages of heterogeneous catalysis, namely the recycling of the system and the possibility to drive selectivity towards desired products. Herein we report a highly porous cellulose-based nanosponge (CNS) and its use as a recoverable catalyst for Henry and Knoevenagel reactions, two classical amino-catalyzed transformations. The material is obtained by cross-linking between TEMPO-oxidized cellulose nanofibers (TOCNF) and branched polyethyleneimine 25 kDa (bPEI) in the presence of citric acid. CNS have been developed as sorbent materials for water remediation but their use as heterogeneous catalysts was never investigated. The fully characterized micro- and nano-porous system guarantees a complete penetration of CNS, allowing reagents to diffuse within. Indeed, by modulating reaction conditions (catalyst loading, temperature, solvent, microwave versus conventional heating, relative ratio of reagents) it was possible to drive selectivity towards the desired products, while maintaining high efficiency in terms of conversion. The catalyst could be re-used several times without losing in catalytic efficiency. In most cases the products’ distribution is quite different from homogeneous conditions, this much more emphasizing the importance of this heterogeneous solution.
Riva, Laura,Punta, Carlo,Sacchetti, Alessandro
p. 6214 - 6222
(2020/10/02)

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation
A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.
Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew
p. 346 - 364
(2019/01/08)

A chiral bicyclic skeleton-tethered bipyridine-Zn(OTf)2 complex as a Lewis acid: Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
A conformationally rigid chiral bicyclic skeleton tethered bipyridine-Zn(OTf)2 complex facilitated the enantioselective Friedel-Crafts alkylation of indoles with trans-β-nitroarylalkenes in an enantioselective manner at elevated temperature. Indoles reacted smoothly with β-nitroarylalkenes to generate the corresponding 3-(2-nitroalkyl)indoles in good to excellent yields (up to 94%) with moderate to excellent enantioselectivities (up to 91%). The stereochemical outcome of the product from indole and trans-β-nitrostyrene in the presence of the CRCB tethered bipyridine-Zn(OTf)2 complex and the DFT calculation of the CRCB tethered bipyridine-Zn:trans-β-nitrostyrene complex support the si-face attack of indole on trans-β-nitrostyrene.
Venkatanna, Kesa,Yeswanth Kumar, Santhakumar,Karthick, Muthupandi,Padmanaban, Ramanathan,Ramaraj Ramanathan, Chinnasamy
p. 4077 - 4086
(2019/04/30)

Facile Synthesis of 1,3,5-Triarylbenzenes and 4-Aryl-NH-1,2,3-Triazoles Using Mesoporous Pd-MCM-41 as Reusable Catalyst
We report mesoporous nano-Pd-MCM-41 catalyzed rapid and efficient synthesis of 1,3,5-triarylbenzenes via de-nitrative cyclotrimerization of β-nitrostyrenes. All the reactions were very fast and high yielding. The Pd-MCM-41 was also very effective in catalyzing de-nitrative [3+2] cycloaddition of β-nitrostyrenes with TMSN3 to synthesize 4-aryl-NH-1,2,3-triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.
Saha, Arijit,Wu, Chia-Ming,Peng, Rui,Koodali, Ranjit,Banerjee, Subhash
p. 104 - 111
(2019/01/04)

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
supporting information
p. 16490 - 16494
(2019/11/03)

Cinnamic acid derivative and preparation method and application thereof
The invention provides a cinnamic acid derivative. The cinnamic acid derivative is of the structure as shown in the formula I. The invention also provides two methods for preparing the cinnamic acid derivative. The two methods depend on a single bond or double bonds in the structure shown in the formula I. The invention further provides a pesticide. The pesticide comprises the cinnamic acid derivative. In addition, the invention provides a sterilization method. The sterilization method includes the step of applying the cinnamic acid derivative or the pesticide to crops. The crops include rice,wheat, fruit trees and vegetables. The low-toxicity, low-residue-content and high-activity environment-friendly cinnamic acid derivative is developed, and the cinnamic acid derivative pesticide can replace traditional high-toxicity and high-residue-content pesticides.
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Paragraph 0187-0190

(2019/10/22)

One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity
Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.
Alishetty, Suman,Shih, Hong-Pin,Han, Chien-Chung
p. 2513 - 2516
(2018/05/17)

Highly Enantioselective Michael Addition of Dithiomalonates to Nitroolefins Catalyzed by New Bifunctional Chiral Thioureas
We report a highly efficient asymmetric Michael addition of dithiomalonates to trans -β-nitroole?ns catalyzed by versatile cinchona-based bifunctional thioureas, which provides the corresponding adducts in high yields (up to 92%) and with excellent enanti
Yuan, Jia-Ni,Liu, Hui-Xia,Tian, Qin-Qin,Ji, Nan,Shen, Kuo,He, Wei
supporting information
p. 2577 - 2586
(2018/05/03)

Fe(III)/Pyridine-Mediated Decarboxylative Nitration of α,β-Unsaturated Acids with Iron Nitrate
A novel and efficient method for the synthesis of (E)-nitroolefins in moderate to excellent yields is developed by Fe(III)/pyridine-mediated decarboxylative nitration of α,β-unsaturated acids with iron nitrate. A series of α,β-unsaturated acids are well tolerated in this procedure.
Yang, Zan,Li, Jiao,Hua, Jie,Yang, Tao,Yi, Jianmin,Zhou, Congshan
supporting information
p. 1079 - 1082
(2017/05/19)

Multicomponent synthesis of 4-aryl-NH-1,2,3-triazoles in the presence of Al-MCM-41 and sulfated zirconia
The acid properties of Al-MCM-41 and sulfated zirconia were used to develop a strategy for the synthesis of 4-aryl-NH-1,2,3-triazoles via a multicomponent reaction involving various benzaldehydes, sodium azide and nitromethane. The efficiency of the process is analysed from the perspective of the difference in acids among the catalysts used.
Vergara-Arenas, Blanca Ivonne,Lomas-Romero, Leticia,ángeles-Beltrán, Deyanira,Negrón-Silva, Guillermo Enrique,Gutiérrez-Carrillo, Atilano,Lara, Víctor Hugo,Morales-Serna, José Antonio
supporting information
p. 2690 - 2694
(2017/06/23)

Metal-free radical trifluoromethylation of β-nitroalkenes through visible-light photoredox catalysis
A catalytic method for functional group interconversion is immensely important in modern sciences. Here, we report an efficient catalytic conversion of nitroalkenes to highly stereoselective 1-trifluoromethylalkenes at room temperature. This unprecedented metal-free photocatalytic strategy is simple and operates under visible-light irradiation using the commercially available CF3 source.
Midya, Siba P.,Rana, Jagannath,Abraham, Thomas,Aswin, Bhaskaran,Balaraman, Ekambaram
supporting information
p. 6760 - 6763
(2017/07/10)

Tetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag
Tetraarylphosphonium inner-salts (TAPIS) have been designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst has been successfully applied in Michael addition, cyanation and trifluoromethylation reactions.
Guo, Shuhui,Mi, Xueling
supporting information
p. 2881 - 2884
(2017/07/11)

Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins
Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins is described. A series of 2-((2-nitro-1-arylethyl)thio)pyrimidines were efficiently synthesized. The protocol has advantages of wide range of substituents tolerance, no catalyst, additives and bases, mild condition, and high yield. The method can also extend to gram scale.
Li, Zheng,Song, Geyang,He, Jiaojiao,Du, Yan,Yang, Jingya
p. 686 - 698
(2017/09/06)

Cu(NO3)2-catalyzed nitrodecarboxylation of α,β-unsaturated acids: facile synthesis of (E)-nitroolefins under additive-free conditions
Abstract: An additive-free, facile, efficient, and ecofriendly protocol for synthesis of (E)-nitroolefins via nitrodecarboxylation of α,β-unsaturated acids has been developed. Cu(NO3)2 was used as both nitrating agent and catalyst. Furthermore, the presented methodology offers several advantages such as easily accessible and stable substrates, inexpensive catalyst, high to excellent yield, short reaction time, and simple posttreatment procedure. Graphical Abstract: [Figure not available: see fulltext.]
Luo, Zai-Gang,Xu, Feng,Fang, Yu-Yu,Liu, Peng,Xu, Xue-Mei,Feng, Cheng-Tao,Li, Zhong,He, Jie
p. 6079 - 6087
(2016/06/01)

Yolk-shell-structured mesoporous silica: A bifunctional catalyst for nitroaldol-Michael one-pot cascade reaction
Great interest in heterogeneous asymmetric catalysis has focused on obtaining an enantioselective cascade reaction through a controllable active site-isolated heterogeneous catalyst. Herein, we utilize a yolk-shell-structured mesoporous silica and assemble an active site-isolated bifunctional heterogeneous catalyst, where chiral cinchonine-based squaramide molecules are anchored within a silicate channel as an outer shell while amine-functionalities are entrapped onto a silicate yolk as an inner core. Structural analyses and characterizations of the heterogeneous catalyst reveal its well-defined single-site chiral active species within its silicate network. Electron microscopy confirms the yolk-shell-structured mesoporous material. As presented in this study, as a bifunctional heterogeneous catalyst, it enables an efficiently nitroaldol-Michael cascade reaction to conduct the three-component coupling of nitromethane, aldehyde and acetylacetone into various chiral diones with high yields and up to 99% enantioselectivities in a one-pot process. As expected, this active site-isolated catalyst not only enhances the catalytic selectivity of the first-step nitroaldol condensation, but also keeps the enantioselectivity of the second-step Michael addition. Moreover, the heterogeneous catalyst can be also recovered easily and recycled repeatedly, making it an interesting feature in a three-component organic transformation.
An, Juzeng,Cheng, Tanyu,Xiong, Xi,Wu, Liang,Han, Bin,Liu, Guohua
p. 5714 - 5720
(2016/07/21)

Palladium(II)-catalyzed C-C and C-O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline: N -oxides and nitroalkenes
C1-Benzoyl isoquinolines can be generated via a palladium(ii)-catalyzed C-C and C-O coupling of isoquinoline N-oxides with aromatic nitroalkenes. The reaction proceeds through remote C-H bond activation and subsequent intramolecular oxygen atom transfer (OAT). In this reaction, the N-O bond was designed as a directing group in the C-H bond activation as well as the source of an oxygen atom.
Li, Jiu-Ling,Li, Wei-Ze,Wang, Ying-Chun,Ren, Qiu,Wang, Heng-Shan,Pan, Ying-Ming
supporting information
p. 10028 - 10031
(2016/08/15)

Synthesis of β-nitrostyrenes in the presence of sulfated zirconia and secondary amines
A simple and efficient protocol for the synthesis of β-nitrostyrenes has been achieved by the use of sulfated zirconia-secondary amine (piperidine, pyrrolidine, proline or prolinol) cooperative systems. The condensation of different aldehydes and nitromethane demonstrates the efficiency of this process, which does not require high-temperature reactivation for the reuse of the catalytic material.
González-Olvera,Vergara-Arenas,Negrón-Silva,Angeles-Beltrán,Lomas-Romero,Gutiérrez-Carrillo,Lara,Morales-Serna
p. 99188 - 99192
(2015/12/05)

An Acid/Base-Regulated Recyclable Strategy for Homogeneous Cinchona Alkaloid-Derived Primary Amine Organocatalysts in Aldol, Vinylogous Michael and Double-Michael Cascade Reactions
A practical, recyclable strategy for homogeneous cinchona alkaloid-derived primary amine organocatalysts was developed by controlling the solubilities in an aqueous/organic biphasic system through regulating the pH of the aqueous phase, effecting the prot
Wan, Jingwei,Zhao, Zhiwei,Wang, Falu,Ma, Xuebing
supporting information
p. 5755 - 5763
(2015/09/15)

Diaminosilane-functionalized on silicate-stabilised hydrotalcite (MA-HTSi-DA): As potential catalyst for nitro-aldol condensation
Diaminosilane was introduced into silicate-anion-intercalated hydrotalcite (HT-Si) using a post-synthesis method. The resulting functionalized materials possess surface basicity. The textural properties of the functionalized materials were systematically investigated through powder XRD, FTIR and MAS-NMR studies. The diamine-functionalized materials showed very good catalytic activity for the nitro-aldol condensation of benzaldehyde and nitromethane under solvent-free conditions. The materials showed comparable catalytic activity upon recycling.
Thangaraj, Baskaran,Jayaraj, Christopher,Srinivasan, Radhakrishnan,Ayyamperumal, Sakthivel
p. 11 - 18
(2015/09/01)

Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agents
A new class of highly substituted pyrroles have been synthesized via a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation. N-Methyl-N-[(E)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM) 1 and β-nitrostyrenes 3 underwent cycloaddition to afford the desired products 4 in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their in vitro anti-bacterial activity. Among the synthesized pyrrole derivatives, 4b, 4c, 4e, 4g, 4i, 4j, 4l, 4m and 4n displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.
Balachandra, Biguvu,Shanmugam, Sivakumar,Muneeswaran, Thillaichidambaram,Ramakritinan, Muthiah
p. 64781 - 64789
(2015/08/18)

1,4-addition of TMSCCl3 to nitroalkenes: Efficient reaction conditions and mechanistic understanding
Improved synthetic conditions allow preparation of TMSCCl3 in good yield (70 %) and excellent purity. Compounds of the type NBu4X [X=Ph3SiF2 (TBAT), F (tetrabutylammonium fluoride, TBAF), OAc, Cl and Br] act as catalytic promoters for 1,4-additions to a range of cyclic and acyclic nitroalkenes, in THF at 0-25 °C, typically in moderate to excellent yields (37-95 %). TBAT is the most effective promoter and bromide the least effective. Multinuclear NMR studies (1H, 19F, 13C and 29Si) under anaerobic conditions indicate that addition of TMSCCl3 to TBAT (both 0.13 M) at -20 °C, in the absence of nitroalkene, leads immediately to mixtures of Me3SiF, Ph3SiF and NBu4CCl3. The latter is stable to at least 0 °C and does not add nitroalkene from -20 to 0 °C, even after extended periods. Nitroalkene, in the presence of TMSCCl3 (both 0.13 M at -20 °C), when treated with TBAT, leads to immediate formation of the 1,4-addition product, suggesting the reaction proceeds via a transient [Me 3Si(alkene)CCl3] species, in which (alkene) indicates an Si O coordinated nitroalkene. The anaerobic catalytic chain is propagated through the kinetic nitronate anion resulting from 1,4 CCl3 - addition to the nitroalkene. This is demonstrated by the fact that isolated NBu4[CH2=NO2] is an efficient promoter. Use of H2C=CH(CH2)2CH=CHNO 2 in air affords radical-derived bicyclic products arising from aerobic oxidation. Understanding TMSCCl3: The synthesis and reactivity of TMSCCl3 has been investigated. The mechanism of 1,4-CCl3 addition to nitroalkenes begins with nitroalkene coordination, followed by the attack of an external fluoride ion, and does not involve the formation of NBu4[Me3SiFCCl3] (see figure).
Wu, Na,Wahl, Benoit,Woodward, Simon,Lewis, William
p. 7718 - 7724
(2014/07/07)

Probing the evolution of an Ar-BINMOL-derived salen-Co(iii) complex for asymmetric Henry reactions of aromatic aldehydes: Salan-Cu(ii) versus salen-Co(iii) catalysis
A new type of chiral salen-Co catalyst that features aromatic π-walls and an active Co(iii) center has been developed for enantioselective Henry/nitroaldol reactions on the basis of salen-Cu catalysis. The asymmetric Henry reaction of aromatic aldehydes a
Wei, Yun-Long,Yang, Ke-Fang,Li, Fei,Zheng, Zhan-Jiang,Xu, Zheng,Xu, Li-Wen
p. 37859 - 37867
(2014/11/07)

Probing the evolution of an Ar-BINMOL-derived salen-Co(iii) complex for asymmetric Henry reactions of aromatic aldehydes: Salan-Cu(ii) versus salen-Co(iii) catalysis
A new type of chiral salen-Co catalyst that features aromatic π-walls and an active Co(iii) center has been developed for enantioselective Henry/nitroaldol reactions on the basis of salen-Cu catalysis. The asymmetric Henry reaction of aromatic aldehydes a
Wei, Yun-Long,Yang, Ke-Fang,Li, Fei,Zheng, Zhan-Jiang,Xu, Zheng,Xu, Li-Wen
p. 37859 - 37867
(2014/12/11)

17a-HYDROXYLASE/C17,20-LYASE INHIBITORS
The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.
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(2014/03/21)

Highly efficient iridium-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins
The first highly efficient Ir-catalyzed enantioselective hydrogenation of β-acylamino nitroolefins is reported. This reaction provides straightforward access to chiral β-amino nitroalkanes in high yields and excellent enantioselectivities (up to >99.9% ee) catalyzed by an Ir-(R,R)-f-spiroPhos complex. This journal is
Yan, Qiaozhi,Liu, Man,Kong, Duanyang,Zi, Guofu,Hou, Guohua
supporting information
p. 12870 - 12872
(2014/12/11)

Tertiary amine functionalized polyacrylonitrile fiber catalyst for the synthesis of tetrahydrothiophenes
A tertiary amine immobilized fiber was prepared and used to efficiently catalyze tandem Michael-intramolecular Henry reactions between 1,4-dithiane-2,5-diol and trans-β-nitrostyrenes to form the corresponding tetrahydrothiophene derivatives. This newly developed fiber catalyst is applicable to a wide range of trans-β-nitroalkenes and affords good to excellent yields (75-93%) under mild conditions (with 2.5 mol % fiber catalyst at 50 °C in ethanol for 5 h). The fiber catalyst exhibits excellent recyclability and reusability (up to 10 times) after simple workup procedure with only a slight loss in catalytic activity. It is noteworthy that the major diastereomers have r-R, trans-nitro, trans-hydroxy configurations with diastereoselectivities of up to 15:1. This differs from the results obtained when the same reaction is catalyzed by a homogeneous catalyst. This is the first example of a fiber catalyst exhibiting excellent diastereoselectivity.
Xu, Changzhu,Du, Jianguo,Ma, Lichao,Li, Guowei,Tao, Minli,Zhang, Wenqin
supporting information
p. 4749 - 4757
(2013/06/27)

Asymmetric palladium(II)-catalyzed cascade reaction giving quaternary amino succinimides by 1,4-addition and a nef-type reaction
Simple starting materials, high-value products: A dinuclear ferrocene-based PdII complex transforms mixtures of racemic N-benzoyl α-amino acids, nitroolefins, acetic anhydride, and manganese acetate into biologically interesting quaternary amin
Weber, Manuel,Frey, Wolfgang,Peters, Rene
supporting information
p. 13223 - 13227
(2014/01/06)

SAR based design of nicotinamides as a novel class of androgen receptor antagonists for prostate cancer
Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement. AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.
Yang, Su Hui,Song, Chin-Hee,Van, Hue Thi My,Park, Eunsook,Khadka, Daulat Bikram,Gong, Eun-Yeung,Lee, Keesook,Cho, Won-Jea
supporting information
p. 3414 - 3418
(2013/06/05)

A branched domino reaction: Asymmetric organocatalytic two-component four-step synthesis of polyfunctionalized cyclohexene derivatives
Take two: By employing two equivalents of an aldehyde in an asymmetric organocatalytic domino reaction, the nucleophilic enamine intermediate is also converted into the corresponding iminium species through oxidation with o-iodoxybenzoic acid. Thus, polyfunctionalized cyclohexene derivatives are formed from two simple starting materials in good yields and stereoselectivities (see scheme; Bn=benzyl, EWG=electron-withdrawing group). Copyright
Zeng, Xiaofei,Ni, Qijian,Raabe, Gerhard,Enders, Dieter
supporting information
p. 2977 - 2980
(2013/04/11)

Ethylenediamine: A highly effective catalyst for one-pot synthesis of aryl nitroalkenes via henry reaction and dehydration
Ethylenediamine (H2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1%-2% (mol%) of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various arylnitroalkenes 1a-1y in 85%-97% yields. Ethylenediamine (H 2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1-2 mol% of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various aryl nitroalkenes 1a-1y in 85%-97% yields. Copyright
Yang, Jianxin,Dong, Jing,Lue, Xia,Zhang, Qiang,Ding, Wei,Shi, Xiaoxin
p. 2827 - 2833
(2013/08/23)

17α-HYDROXYLASE/C17,20-LYASE INHIBITORS
The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.
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Page/Page column 53-54

(2012/04/04)

Enantio- and diastereoselective Michael additions of C-succinimidyl esters to nitro olefins using cinchonine-derived bifunctional organocatalysts
A novel bifunctional organocatalytic Michael addition of a succinimide-derived pronucleophile to nitro olefins is described. The use of a range of nitro olefins afforded Michael adducts containing contiguous quaternary and tertiary stereogenic centres in
Jakubec, Pavol,Cockfield, Dane M.,Hynes, Peter S.,Cleator, Ed,Dixon, Darren J.
experimental part
p. 1147 - 1155
(2011/10/12)

One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt
One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, and alkyl aldehydes were converted into γ-nitroaldehydes via in situ generation of nitroalkenes.
Yoshida, Masanori,Kitamikado, Naoki,Ikehara, Hiroto,Hara, Shoji
experimental part
p. 2305 - 2309
(2011/06/11)

Facile and efficient michael addition of indole to nitroolefins catalyzed by zn(OAc)22H2O
The Zn(OAc)22H2O-catalyed Michael addition reaction of indole to electron-deficient nitroolefins to afford the corresponding adducts in good to excellent yields with high selectivity is reported.
Ji, Xiang,Tong, Haibo,Yuan, Yu
experimental part
p. 372 - 379
(2011/04/16)

Biocatalytic enantioselective approach to 3-aryl-2-nitropropanols: Synthesis of enantioenriched (R)-5-methoxy-3-aminochroman, a key precursor to the antidepressant drug Robalzotan
The results of our studies on the biocatalytic enantioselective synthesis of different 3-aryl-2-nitropropanols are presented. These compounds could be obtained in moderate to good ee both bybaker's yeast mediated reduction of (E)-2-nitro-3-arylprop-2-en-1-ol precursors and by lipase kinetic resolution of racemic 3-aryl-2-nitropropanols. The synthesis of enantioenriched (R)-5-methoxy-3-aminochroman is also achieved. This important moietyispresent in different molecules active toward the central nervous system and is also the precursor for the synthesis of Robalzotan (NAD299), a potent 5-HT1A antagonist.
Fuganti, Claudio,Sacchetti, Alessandro
experimental part
p. 276 - 284
(2010/11/18)

3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitriles for SERT imaging: Chemical synthesis, evaluation in vitro and radiofluorination
Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as 18F-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful 18F-fluoroalkylation of one pair of compounds are described herein.
Funke, Uta,Fischer, Steffen,Hiller, Achim,Scheunemann, Matthias,Deuther-Conrad, Winnie,Brust, Peter,Steinbach, Joerg
scheme or table
p. 4727 - 4730
(2009/04/08)

A very mild access to 3,4-dihydroisoquinolines using triphenyl phosphite-bromine-mediated bischler-napieralski-type cyclization
Substituted β-phenylethylamides undergo smooth intramolecular cyclization to 3,4-dihydroisoquinolines in good to excellent yields when treated with bromotriphenoxyphosphonium bromide at -60°C in dichloromethane in the presence of triethylamine. The reaction proceeds under the mildest conditions ever reported for Bischler-Napieralski-type cyclizations. When chlorotriphenoxyphosphonium choride is used, low yields are obtained instead. Georg Thieme Verlag Stuttgart.
Vaccari, Daniele,Davoli, Paolo,Ori, Claudia,Spaggiari, Alberto,Prati, Fabio
experimental part
p. 2807 - 2810
(2009/05/07)

Application of the chiral bis(phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to β-nitroalkenes
(Chemical Equation Presented) Me-DuPHOS monoxide is shown to be a very effective ligand in the enantioselective copper-catalyzed addition of dialkylzinc reagents to β-nitroalkenes providing access to chiral nitroalkanes. The major advantages of this process are high yields, broad and complementary substrate scope, and high enantioselectivities. The effect of achiral dummy ligands as an additive has also been documented.
Cote, Alexandre,Lindsay, Vincent N. G.,Charette, Andre B.
p. 85 - 87
(2007/10/03)

Synthesis of analogs of amathamide A and their preliminary antimicrobial activity
Syntheses of three non-brominated analogs of amathamide A (1), a natural alkaloid isolated from the Tasmanian marine bryozoan Amathia wilsoni, are described. Antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudo
Ramirez-Osuna, Moises,Chavez, Daniel,Hernandez, Lourdes,Molins, Elias,Somanathan, Ratnasamy,Aguirre, Gerardo
p. 295 - 301
(2007/10/03)

Benzazine derivatives as phosphodiesterase 4 inhibitors
Compounds of formula I: wherein A is a heterocycle containing a nitrogen atom and optionally saturated or unsaturated and optionally further substituted by an oxo group (═O); R is: hydrogen, cyano, (C1-4)alkoxycarbonyl, carbamoyl; optionally substituted (C4-7)-cycloalkyl, aryl or heterocycle; (C1-8)alkyl, (C2-8)alkenyl or (C2-8)alkynyl optionally branched and/or substituted by (C4-7) cycloalkyl, aryl or heterocycle; aryloxy, heterocyclyloxy, aryl(C1-4)alkoxy, heterocyclyl(C1-4)alkoxy, amino substituted by one or two (C1-4)alkyl group(s), aryl-amino, heterocyclyl-amino, aryl(C1-4)alkyl-amino, or heterocyclyl(C1-4)alkylamino; Y is methylene or ethylene; W is an optionally substituted aryl or heterocycle; R1is hydrogen, (C4-7)cycloalkyl or a (C2-8)alkyl, (C2-8)alkenyl or (C2-8)alkynyl group optionally substituted by hydroxy, oxo, (C4-7)cycloalkyl, aryl or heterocycle, and optionally interrupted by one or more heteroatom(s) or heterogroup(s); R2is a (C1-6)alkyl or polyfluoro(C1-6)alkyl group; the N→O derivatives of the compounds of formula I and the pharmaceutically acceptable salts thereof. The compounds of formula (I) are PDE 4 inhibitors and may be used in compositions and methods involving PDE 4 inhibition.
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Example 40

(2008/06/13)

One-pot synthesis of trans-β-alkylstyrenes
One-pot synthesis of (E)-alkenes 5 from the reactions of aldehyde 1 and nitromethane 2 in the acetic acid solution and then with triethylborane 4 in the biphase of diethyl ether and aqueous solution in the presence of oxygen in air was reported. Various (E)-alkenes 7 could also be prepared when different kinds of secondary or tertiary alkyl iodides 6 were used under similar conditions.
Liu, Ju-Tsung,Yao, Ching-Fa
p. 6147 - 6150
(2007/10/03)

Potent and selective non-benzodioxole-containing endothelin-A receptor antagonists
The benzodioxole ((methylenedioxy)benzene) group is present in a number of endothelin (ET) receptor antagonists thus far reported. As part of our own endothelin antagonist program we have developed (2R*,3R*,4S*)-1-(N,N- dibutylacetamido)-4-(1,3-benzodioxol-5-yl)-2-(4-methoxyphenyl)pyrrolidine-3- carboxylic acid (A-127722). This is a potent antagonist, binding to the ET(A) and ET(B) receptor subtypes with affinities (IC50) of 0.4 and 520 nM, respectively, and also contains the aforementioned benzodioxole. While this compound was seemingly optimized at its N-terminus, no effort had been directed toward understanding the contributions to binding affinity or receptor subtype selectivity conferred by the benzodioxole. Substitution by 1- or 2-naphthyl yielded weak antagonists. Oxygenated benzenes, such as p- anisyl, were potent compounds with IC50s in the low-nanomolar range. Simple deletion of either of the two oxygen atoms (dihydrobenzofurans) yielded extremely potent agents, possessing subnanomolar affinity for the ET(A) receptor. Additionally, the compounds showed enhanced selectivity, binding to the ET(B) receptor subtype in the micromolar range. This paper describes the development of this novel class of compounds.
Tasker, Andrew S.,Sorensen, Bryan K.,Jae, Hwan-Soo,Winn, Martin,Von Geldern, Thomas W.,Dixon, Douglas B.,Chiou, William J.,Dayton, Brian D.,Calzadila, Samuel,Hernandez, Lisa,Marsh, Kennan C.,WuWong, J. Ruth,Opgenorth, Terry J.
p. 322 - 330
(2007/10/03)

Michael reactions of ascorbic acid, 4th communication: Nitrostyrene as a Michael acceptor toward vitamin C
The nitrostyrene derivatives 1a-m, prepared by the reaction of nitromethane with the appropriate substituted benzaldehyde, were reacted with ascorbic acid in a Michael type reaction to the new compounds 2a-h. The structural assignment of the resulting mixture of diastereomers could be performed by means of two dimensional homo- and heterocorrelated NMR spectroscopy and comparison to known Michael adducts of ascorbic acid. Catalytic hydrogenolysis of 2 a yielded the rearranged compound 7, formed by intramolecular aminolysis in analogy to the rearrangement of the Michael adduct of ascorbic acid and methylvinylketone 3 given in the literature. On testing, the C-nucleoside 7 did not reveal virostatic or cytostatic effects.
Schmidt,Eger
p. 11 - 16
(2007/10/02)

3,10-Dimethoxyprotoberberines
Protoberberines with the unusual 3,10-dimethoxy substitution are synthesized by photocyclization of E- and Z-1-ethylidene-1,2,3,4-tetrahydro-6-methoxy-2-(3-methoxybenzoyl)isoquinolines.
Chinnasamy, Pennamuthiriar,Iwasa, Kinuko,Angerer, Silvia von,Weimar, Christian,Wiegrebe, Wolfgang
p. 790 - 798
(2007/10/02)

Diazaestrones and analogs. I. Pharmacological study and synthesis of heterosteroid analogs to establish structure-analgesic activity relationships
With the intention of showing the effect, about pharmacological properties, in replacing two estron asymetric carbon by nitrogen atoms and removal of angular methyl from steroid, stereospecific synthesis of 8,13-diazaestron and several substituted similar compounds was realized from β-1-(succinimidoethyl)-dihydroisoquinolines, precursors of a C open ring synthesis. The splitting of the 2-methoxydiazaestron methyl ester was carried out by mean of binaphthylphosphoric acid, and synthesis of several modified analogs of heterosteroid, was carried out to determine the effect of aromatic ring reduction, lactamic carbonyl reduction, and distance between 8 and 13 nitrogen atoms, about pharmacological activity. Hormonal, spasmolytic and analgesic activities were studied, good results were observed in analgesic activity.
Hocquaux,Marcot,Redeuilh,et al.
p. 319 - 329
(2007/10/02)