cas 5443-49-2, 2-Bromocinnamaldehyde | Articles data

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Synthesis, X-ray crystal structure, electrochemical and antibacterial activity of a silver(I) complex with α-bromo-cinnamaldehyde salicylhydrazone
The mononuclear silver(I) complex [AgL(HL)· DMF] (I) (HL = C 6H13O2N2Br) has been prepared and characterized by physicochemical and spectroscopic methods, single crystal X-ray diffraction, cyclic voltammetry, and antibacterial activity tests. The complex crystallized in the triclinic system, and each Ag(I) is six-coordinate with a distorted octahedral geometry. The ligands chelate the metal center with N, O, and Br atoms from two different Schiff base ligands. O- H···O intermolecular hydrogen bonds connect adjacent complex molecules to form zigzag one-dimensional linear chains along the b axis. Cyclic voltammetry showed that the complex displays an irreversible reduction process at -0.41 V. The data from antibacterial activity tests indicate that the complex inhibits the growth of Staphyloccus aureus and Bacillus subtilis Cohn. Springer Science+Business Media B.V. 2010.
Liu, Jun An,Li, Qing,Wang, Ming Ming,Wang, Hui,Gan, Guo Qing,Qu, Yang,Lin, Zhi Dong
p. 507 - 511
(2010)
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Preparation method for catalytic synthesis of dihydropyrone compound containing 1, 3-enyne functional group by N-heterocyclic carbene
The invention discloses a preparation method for catalytic synthesis of dihydropyrone compound containing 1, 3-enyne functional group by N-heterocyclic carbene, which is characterized in that the derivative is shown as a general formula (1), in the formula, R1 is phenyl, substituted benzene, naphthalene, furan, thiophene or alkyl; R2 is phenyl, substituted benzene, furan or thiophene; and R3 is phenyl, substituted benzene, thiophene or alkyl. The dihydropyrone compound containing 1,3-enyne functional group can be effectively and efficiently prepared from reactant molecules alpha, beta-unsaturated aldehyde and 1,3-enyne aldehyde with simple structural units under the catalysis of N-heterocyclic carbene, and the dihydropyrone derivative has the advantages of good substrate universality, excellent yield, high enantioselectivity and the like.
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Paragraph 0014; 0016

(2021/01/12)

Enantioselective NHC-Catalyzed [3+3] Annulation of α-Bromoenals with 2-Aminobenzimidazoles
A chiral carbene-catalyzed [3+3] annulation of α-bromoenals with 2-aminobenzimidazoles providing pyrimido[1,2-a]benzimidazoles has been described. This protocol features a broad scope and good functional group tolerance. Biological studies indicated that the formed pyrimido[1,2-a]benzimidazole exhibited moderate cytotoxic activity against tumor cells.
Xie, Yangxi,Li, Luoyuan,Sun, Shaofa,Wu, Zijun,Lang, Ming,Jiang, Di,Wang, Jian
supporting information
p. 391 - 394
(2020/01/31)

Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Cyclization–[4+3] Annulation Cascades between 2-(1-Alkynyl)-2-alken-1-ones and Anthranils
This work reports gold-catalyzed [4+3]-annulations of 2-(1-alkynyl)-2-alken-1-ones with anthranils to yield epoxybenzoazepine products with excellent exo-diastereoselectivity (dr>25:1). The utility of this new gold catalysis is manifested by applicable substrates over a broad scope. More importantly, the enantioselective versions of these [4+3]-cycloadditions have been developed satisfactorily with chiral gold catalysts under ambient conditions (DCM, 0 °C); the ee levels range from 88.0–99.9 %. With DFT calculations, we postulate a stepwise pathway to rationalize the preferable exo-stereoselection.
Chao, Tzu-Hsuan,Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information
p. 10396 - 10400
(2020/04/29)

NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones
The unprecedented enantioselective NHC-catalyzed [3 + 3] annulation of α-bromoenals with amidines via a dual C-N bond formation is described. The protocol allows a rapid preparation of 5,6-dihydropyrimidinones in acceptable yields with good enantioselectivities.
Meng, Di,Xie, Yangxi,Peng, Qiupeng,Wang, Jian
supporting information
p. 7635 - 7639
(2020/10/09)

Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: N-versus C-Attack Paths
Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.
Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information
p. 8229 - 8233
(2020/11/03)

Crystal structure, characterization, Hirshfeld surface analysis and DFT studies of two [propane 3-bromo-1-(triphenyl phosphonium)] cations containing bromide (I) and tribromide (II) anions: The anion (II) as a new brominating agent for unsaturated compounds
In this study, propane 3-bromo-1- (triphenyl phosphonium) bromide, I, and propane 3-bromo-1- (triphenyl phosphonium) tribromide, II, (II as a new brominating agent) were synthesized and characterized by 1H NMR, 13C NMR, 31P NMR, FT-IR, spectroscopy, Thermogravimetric Analysis, Differential thermal analysis, Differential scanning calorimetry and single crystal X-ray analysis. Density functional theory calculations (energy, structural optimization and frequencies, Natural Bond Orbital, absorption energy and binding energy) were performed by using B3LYP/6-311 G++ (d, p) level of theory. Hirshfeld surface analysis and fingerprint plots were utilized to investigate the role of bromide and tribromide anions on the crystal packing structures of title compounds. The results revealed that the change of accompanying anionic moiety can affect the directional interactions of C-H?Br hydrogen bonds between anionic and cationic units in which the H?Br with a proportion of 53.8% and 40.9% have the major contribution in the stabilization of crystal structures of I and II, respectively. Furthermore, the thermal stability of new brominating agent II with tribromide anion was compared with compound I with bromide anion. Nontoxicity, short reaction time, thermal stability, simple working up and high yield are some of the advantages of these salts.
Nokhbeh, Seyed Reza,Gholizadeh, Mostafa,Salimi, Alireza,Sparkes, Hazel A.
p. 542 - 554
(2019/06/18)

Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles
A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.
Zhang, Dongsheng,Fan, Yingzhu,Yan, Zhongliang,Nie, Yi,Xiong, Xingquan,Gao, Lizhu
supporting information
p. 4211 - 4216
(2019/08/07)

N-Heterocyclic Carbene-Catalyzed β-Indolylation of α-Bromoenals with Indoles
An unprecedented example of NHC-catalyzed β-indolylation of α-bromoenals with indoles has been developed. This concise protocol features several advantages (mild reaction conditions, broad substrate scope) and constructs synthetically useful building blocks, namely β-biaryl methylene esters. Notably, the β-biaryl methylene-type fragment is widely found in natural products or pharmaceuticals. (Figure presented.).
Sun, Shaofa,Lang, Ming,Wang, Jian
p. 5704 - 5708
(2019/12/24)

A method for synthesis of α - bromo cinnamic aldehyde
The invention discloses a method for synthesis of α - bromo cinnamic aldehyde, the first is the preparation of silica gel supported bromine; then to carbon tetrachloride as solvent, cinnamic aldehyde with silica gel supported bromine addition reaction for the synthesis of 2, 3 - dibromo - 3 - phenyl propanal; finally 2, 3 - dibromo - 3 - phenyl-propionaldehyde in phase transfer catalyst under the effect of the elimination reaction with the sodium carbonate in the synthetic α - bromo cinnamic aldehyde. The invention has the high reaction yield, the product quality is good, the after-treatment process is simple.
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Paragraph 0036; 0042-0049; 0056-0061

(2019/05/15)

N-Heterocyclic Carbene-Catalyzed Enantioselective β-Amination of α-Bromoenals Enabled by a Proton-Shuttling Strategy
An unprecedented enantioselective NHC-catalyzed β-amination of α-bromoenals with o-benzodiamines was developed by utilizing a proton-shuttling strategy. This formal [4+3] annulation protocol yielded the corresponding 1,5-benzodiazepines in high yields with excellent enantioselectivities. The obtained optically active 1,5-benzodiazepines as building blocks and pharmacophores should be useful in the synthesis of other valuable molecules or in drug discovery.
Lang, Ming,Wang, Jian
supporting information
p. 2958 - 2962
(2018/06/27)

Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines
The reactions of trifluoromethylated 2-bromoenones and N,N′-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.
Muzalevskiy, Vasily M.,Ustynyuk, Yury A.,Gloriozov, Igor P.,Chertkov, Vyacheslav A.,Rulev, Alexander Yu.,Kondrashov, Evgeniy V.,Ushakov, Igor A.,Romanov, Alexey R.,Nenajdenko, Valentine G.
p. 16982 - 16989
(2015/11/16)

Nucleophilic carbene-catalyzed redox-esterification reaction of α-halo-α,β-unsaturated aldehyde
A nucleophilic carbene catalyzed redox esterification between α-halo-α,β-unsaturated aldehydes and various alcohols has been developed. Interestingly, the reaction provided α,β-unsaturated esters instead of the saturated α-halo substituted esters as the only product in good to high yield with excellent trans-selectivity, presumably via the umpolung-halo-elimination pathway.
Wang, Xiang-Bo,Zou, Xiao-Lei,Du, Guang-Fen,Liu, Zhi-Yong,Dai, Bin
experimental part
p. 6498 - 6503
(2012/08/27)

N-heterocyclic carbene catalyzed reactions of α-bromo-α,β- unsaturated aldehydes/α,β-dibromoaldehydes with 1,3-dinucleophilic reagents
Carbenes ring true: N-Heterocyclic carbene (NHC) catalyzed reactions of α-bromo-α,β-unsaturated aldehydes/α,β- dibromoaldehydes with 1,3-dinucleophilic reagents, such as 1,3-dicarbonyl compounds, β-enamino ketones, and β-enamino esters through umpolung processes gave functionalized 3,4-dihydropyranones and 3,4-dihydropyridinones (see scheme). The availability of the starting materials, lack of external oxidant, and usefulness of the products make this strategy attractive.
Yao, Changsheng,Wang, Donglin,Lu, Jun,Li, Tuanjie,Jiao, Weihui,Yu, Chenxia
supporting information; experimental part
p. 1914 - 1917
(2012/03/22)

Organocatalytic diastereoselective dibromination of alkenes
A highly diastereoselective pyrrolidine-promoted dibromination of alkenes by combination of NBS and succinimide is presented. The pyrrolidine-mediated dibromination of alkenes is higly anti-selective and gives the corresponding products in moderate to high yields and up to >25:1 dr.
Zhu, Mingzhao,Lin, Shuangzheng,Zhao, Gui-Ling,Sun, Junliang,Córdova, Armando
scheme or table
p. 2708 - 2712
(2010/07/04)

DERIVATIVES OF 5,9-METHANOCYCLOOCTA[B]PYRIDIN-2-(1H)-ONE, THEIR PREPARATION AND USE AS ANALGESICS
A compound of Formula I, a pharmaceutically-acceptable salt or a hydrate thereof, wherein R1 is H, or C1-4 alkyl; R2 is H, halogen, or C1, alkyl; R3 is H, halogen, or C1-4 alkyl, and R4 is C1-6 alkyl, aryl; or ═CR3R4 is cyclopentylidene, cyclohexylidene, 1-methylpiperidin-4-ylidene, or inden-1-ylidene; R5 is independently at each occurrence F, Cl, Br, CF3, R9, OR9, NR9R10, NO2, CN, COOR9, O2CR9, CONR9R10, NR9C(O)R10, heterocyclic group, aryl, or a group of Formula II; R6 is H, halogen, or C1-4 alkyl; R7 is H, halogen, or C1-4 alkyl; R8 is H, C1, alkyl group; R9 is H, or C1-6 alkyl; R10 is H, or C1-6 alkyl; R11 is H, or C1-4 alkyl; R12 is H, or C1-4 alkyl; m is 0, 1, or 2; when R5 is F, Cl, Br, CF3, R9, OR9, NR9R10, NO2, CN, COOR9, O2CR9, CONR9R10, NR9C(O)R10, heterocyclic group, or aryl, n is 1, 2, 3, or 4; when R5 is the group of Formula II, n is 0, 1, 2, 3, or 4; x is 0, 1, 2, 3, or 4.
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Page/Page column 17

(2009/05/28)

ANALGESIC 5, 9 - METHANOCYCLOOCTA (b) PYRIDIN - 2 (1H) - ONE DERIVATIVES, THEIR PREPARATION METHOD AND USE
Compounds represented by the Formula I or salts, hydrates thereof, wherein R1, R8, R11 and R12 are H or C1-4 hydrocarbonyl respectively; R2, R3, R6 and R7 are H, halogen or C1-4 hydrocarbonyl respectively; R4 is C1-6 hydrocarbonyl or Ar; or =CR4R3 is cyclopentylidene, cyclohexylidene, 1-methylpiperidyl-4-idene or indenyl-1-idene; R5 is H, 1-4 same or different F, Cl, Br, CF3, R9, OR9, NR9R10, NO2, CN, COOR9, O2CR9, CONR9R10, NR9C(O)R10, heterocyclic, aryl or groups represented by the Formula II respectively; R9 and R10 are H or C1-6 hydrocarbonyl; Ar is aromatic ring; m is 0, 1 or 2; n is 0, 1, 2, 3 or 4, for treating mammal pain, functional painful syndrome, organic painful syndrome or tissue painful syndrome, and their preparation method.
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Page/Page column 16

(2009/04/23)

Process development of a novel non-xanthine adenosine A1 receptor antagonist
(+)-(R)-1-[(E)-3-(2-phenylpyrazolo[l,5-a]pyridin-3-yl)acryloyl]-2- piperidine ethanol (FK453) is a novel, potent adenosine AI receptor antagonist for the regulation of renal function. The development of a reliable process suitable for large scale manufacture is described. A Horner-Emmons reaction and a 1,3-dipolar cycloaddition were successfully scaled up to afford ethyl (E)-3-(2-phenylpyrazolo[l,5-a]pyridin-3-yl)acryloylate, with excellent regioselectivity and stereoselectivity. Process improvements and optimization of each step permitted elimination of column chromatography, resulting in a straightforward, practical synthesis of FK453.
Zanka, Atsuhiko,Uematsu, Ryoichi,Morinaga, Yasuhiro,Yasuda, Hironobu,Yamazaki, Hiroshi
p. 389 - 393
(2013/09/08)

Oxidation of α,β-enones and alkenes with oxone and sodium halides: A convenient laboratory preparation of chlorine and bromine
Mixtures of oxone and sodium chloride or sodium bromide afford solutions of chlorine or bromine, respectively. These solutions effectively add chlorine and bromine to α,β-enones and alkenes. The method affords improved yields of 3-alkyl-2-halo-2-cycloalkenones which are sometimes difficult to prepare.
Dieter, R. Karl,Nice, Lois E.,Velu, Sadanandan E.
p. 2377 - 2380
(2007/10/03)

ELECTROPHILIC REACTIONS OF HALIDES OF GROUP VI ELEMENTS. VII. REACTIONS OF SELENIUM TETRAHALIDES WITH STYRENE AND ITS β-SUBSTITUTED DERIVATIVES
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Migalina, Yu. V.,Galla-Bobik, S. V.,Lendel, V. G.,Staninets, V. I.
p. 1380 - 1382
(2007/10/02)

Reactivity of hypophosphites IV. Reactions of alkyl hypophosphites with α-bromocinnamaldehyde
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Yudelevich, V. I.,Solonkina, I. V.,Sokolov, L. B.,Ionin, B. I.,Komarov, E. V.,et al.
p. 696 - 702
(2007/10/02)

A CONVENIENT PREPARATION OF 2-HALOENONES FROM ENONES USING PHENYLSELENIUM HALIDES
Enones can be converted in high yield to their corresponding 2-halo analogues by treatment with an excess of phenylselenium halide in methylene chloride/pyridine at 37 deg C.
Ley, Steven V.,Whittle, Alan J.
p. 3301 - 3304
(2007/10/02)