- KF-Al2O3 induced the condensation of 2-nitrofluorene and para-substituted acetophenones with aromatic aldehydes
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In the presence of KF-Al2O3 as a solid base, 2-nitrofluorene 1 condensed with aromatic aldehydes 2a-f in methanol to give 2-nitrodibenzofulvenes 3a-f in high yield. The para-substituted acetophenones 4a-f reacted with cinnamic aldehyde to give 1, 5-diaryl-2, 4-pentadien-1-ones 6a-f in moderate yield.
- Yan,Sun
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- Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation
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A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.
- Yu, Bangkui,Gao, Bao,Zhang, Xuexia,Zhang, Haocheng,Huang, Hanmin
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supporting information
p. 566 - 570
(2021/02/01)
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- Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
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The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.
- Li, Chunsheng,Li, Meng,Zhong, Wentao,Jin, Yangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 872 - 875
(2019/05/16)
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- Antibacterial & antitubercular activities of cinnamylideneacetophenones
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Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory
- Polaquini, Carlos R.,Torrezan, Guilherme S.,Santos, Vanessa R.,Nazaré, Ana C.,Campos, Débora L.,Almeida, Laíza A.,Silva, Isabel C.,Ferreira, Henrique,Pavan, Fernando R.,Duque, Cristiane,Regasini, Luis O.
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supporting information
(2017/11/07)
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- Highly regioselective introduction of aryl substituents via asymmetric 1,4-addition of boronic acids to linear α,β,γ,δ-unsaturated ketones
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An efficient palladium(II)-catalyzed regioselective asymmetric 1,4-conjugate addition of arylboronic acids to linear α,β,γ,δ-unsaturated ketones is developed using phosphapalladacycle catalysts. The relevant 1,4-products were obtained exclusively with per
- Gan, Kennard,Ng, Jia Sheng,Sadeer, Abdul,Pullarkat, Sumod A.
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supporting information
p. 254 - 258
(2016/01/20)
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- Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids
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In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.
- Roman, Bart I.,De Ryck, Tine,Verhasselt, Sigrid,Bracke, Marc E.,Stevens, Christian V.
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p. 1027 - 1031
(2015/02/19)
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- Synthesis, antimicrobial and cytotoxic activity of novel 1,5 benzodiazepine derivatives
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In the present study, a series of novel 2-(substituted phenyl)-3-styryl-2,3-dihydro- 1H-benzo [b] [1,4] diazepines (1-12) has been synthesized from 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones (1a-12a). 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones were prepared by condensing cinnamaldehyde with various aromatic ketones in the presence of 20% NaOH as base. Different 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones on cyclisation with o-phenylene diamine in the presence of NaOH as base resulted in 2-(substituted phenyl)-3-styryl-2,3-dihydro-1H-benzo [b] [1,4] diazepine derivatives. The structures of the newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR and mass spectroscopic studies. All titled compounds were screened for their antimicrobial and cytotoxic activities. Most of the compounds showed promising cytotoxic, antibacterial and antifungal activities.
- Bhat, K. Ishwar,Kumar, Abhishek,Prathyusha
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p. 161 - 164
(2019/01/16)
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- Iron-catalyzed aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines
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A simple and high yielding method for the synthesis of tri-substituted pyrazoles via iron(III) catalyzed aerobic oxidative aromatization of pyrazolines has been reported. The process demonstrates a variety of functional group tolerance.
- Ananthnag, Guddekoppa S.,Adhikari, Adithya,Balakrishna, Maravanji S.
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p. 240 - 243
(2013/12/04)
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- Synthesis, characterization and biological activity studies of some substituted pyrimidine derivatives
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A new series of substituted 1-phenyl-3-styryl-4,5-dihydo-1H-pyrazoles (TP1-TP9) has been synthesized by the cyclisation of chalcones with phenyl hydrazine and glacial acetic acid and substituted 4-styryl-pyrimidin-2-ols (LP1-LP9) have been synthesized by the condensation of chalcones with urea in the presence of 40% NaOH as a base. The intermediate substituted 1,5-diphenylpenta-2,4-dien-1-ones were synthesized by condensing cinnamaldehyde with various substituted aromatic ketones in presence of 20% NaOH. The title compounds obtained were characterized by IR, 1H NMR, mass spectral data and were screened for antimicrobial, anticancer and antitubercular activity.
- Ishwar Bhat,Kumar, Abhishek,Thara,Kumar, Pankaj
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p. 271 - 276
(2019/01/21)
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- Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones
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A highly regioselective and enantioselective copper-catalyzed 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ- unsaturated ketones was developed. The 1,4-addition products were obtained regioselectively in high yields with up to 98% ee. The Royal Society of Chemistry 2013.
- Ma, Zhenni,Xie, Fang,Yu, Han,Zhang, Yiren,Wu, Xiaoting,Zhang, Wanbin
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supporting information
p. 5292 - 5294
(2013/06/27)
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- Synthesis of substituted fluorenes by cascade allenylation, electrocyclization and intramolecular friedel-crafts reaction of 1,3-diene-substituted propargylic alcohols
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A concise, one-step synthesis of substituted fluorenes through TiCl 4-promoted cascade allenylation, electrocyclization and intramolecular Friedel-Crafts reaction of 1,3-diene-substituted propargylic alcohols has been developed. An interesting substituent-dependent regioselectivity was observed.
- Xu, Xiangsheng,Li, Tao,Li, Xiaoqing,Shao, Jiangbin
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p. 383 - 388
(2013/04/23)
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- Tandem mass spectrometry based investigation of cinnamylideneacetophenone derivatives: Valuable tool for the differentiation of positional isomers
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Cinnamylideneacetophenones have been extensively used as versatile starting materials in numerous different transformations. The structural characterization of this type of compounds is, therefore, of crucial importance since it can give information on th
- Resende, Diana I. S. P.,Silva, Eduarda M. P.,Barros, Cristina,Domingues, M. Rosario M.,Silva, Artur M. S.,Cavaleiro, Jose A. S.
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experimental part
p. 3185 - 3195
(2012/04/10)
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- Iodine-catalysed conjugate addition of indole with α- cinnamylideneketones: Formation of β-(3-indolyl)-α,β-dihydro- α-cinnamylideneketones and bis(3-indolyl)methylbenzene
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β-(3-Indolyl)-α,β-dihydro-α-cinnamylideneketones and bis(3-indolyl)methylbenzene have been obtained in moderate to good yield by conjugate addition of indole with α-cinnamylideneketones under mild reaction condition in dry ethanol using iodine as catalyst. The structures of the products have been established from their spectral data.
- Pal, Rammohan,Mandal, Tapas K.,Mallik, Asok K.
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experimental part
p. 619 - 623
(2011/06/21)
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- Amberlyst-15 catalysed microwave assisted cross-aldol condensation between ketones and aldehydes under solvent free condition
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Amberlyst-15 has been applied as an efficient heterogeneous catalyst for the first time for rapid synthesis of α,α′-bis(arylmethylene) cycloalkanones, α,α′-bis(cinnamylidene)cycloalkanones, ′-cinnamylideneacetophenones and chalcones in very good yield by the reaction between various aldehydes and ketones under microwave irradiation. The new process for the cross-aldol condensation reaction works well in absence of any solvent. The yields are high and the process is environmentally benign.
- Pal, Rammohan,Mandal, Tapas K.,Guha, Chayan,Mallik, Asok K.
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experimental part
p. 711 - 717
(2012/03/11)
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- Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products
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Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
- Zhang, Hong,Jin, Hong,Ji, Lan-Zhu,Tao, Ke,Liu, Wei,Zhao, Hao-Yu,Hou, Tai-Ping
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experimental part
p. 94 - 100
(2012/06/01)
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- Synthesis and biological activity of some 3, 5-diarylisoxazoline derivatives: Reaction of substituted chalcones with hydroxylamine hydrochloride
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A series of 3-aryl-5-styrylisoxazoline/ 3,5-diarylisoxazoline derivatives were synthesized by the reaction of appropriately substituted chalcones and hydroxylamine hydrochloride in presence of alkali in ethanol. The synthesized heterocycles have been characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for biological activity against a variety of test organisms.
- Sharma, Vandana,Sharma
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experimental part
p. 203 - 209
(2011/01/03)
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- Unprecedented consecutive, competitive nucleophilic addition to construct densely functionalized propargylic alcohols
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An efficient one-pot process to construct a series of polyfunctionalized propargylic alcohol derivatives from the simple materials without functional protection was investigated. A solution of nBuLi in hexane was added into dry THF by syringe the resulting solution was then maintained at RT for 3 hours. the freshly prepared lithium enolate of acetaldehyde was used directly in the reaction. The nBuLi was added over a period of 30 minutes by syringe to a solution of terminal alkyne in THF at -30°C. The scope and limitations of the reaction was explored by examining other terminal alkynes. A number of different carbonyl-containing substrates were also examined. It was observed that propargylic alcohol derivatives are important synthetic intermediates in organic synthesis.
- Liu, Jie,An, Yan,Wang, Ya-Hui,Jiang, Hai-Ying,Zhang, Yu-Xin,Chen, Zili
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supporting information; experimental part
p. 9131 - 9134
(2009/09/06)
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- Epoxidation of (E,E)-cinnamylideneacetophenones with hydrogen peroxide and iodosylbenzene with salen-MnIII as the catalyst
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(E,E)-Cinnamylideneacetophenones 3a-j were epoxidized under mild conditions with Jacobsen's catalyst 4 and hydrogen peroxide or iodosylbenzene as oxidants. γ,δ-Monoepoxides and a diastereomeric mixture of α,β:γ,δ-diepoxides were obtained in each case, and
- Santos, Clementina M. M.,Silva, Artur M. S.,Cavaleiro, Jose A. S.,Levai, Albert,Patonay, Tamas
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p. 2877 - 2887
(2008/03/13)
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- Synthesis of some 3-(4-styryl-6-aryl-pyridin-2-yl)- and 3-(6-styryl-4-aryl-pyridin-2-yl) coumarins
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Various 3-(4-styryl-6-aryl-pyridin-2-yl) coumarins 4a-f and 3-(6-styryl-4-aryl-pyridin-2-yl) coumarins 5a-f have been synthesized by the reaction of 3-coumarinoyl methyl pyridinium salt I with pentadienones 2a-f and 3a-f respectectively in the presence of ammonium acetate in refluxing acetic acid.
- Brahmbhatt,Pandya, Urvish R.
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p. 145 - 149
(2007/10/03)
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- Synthesis of 3-benzoyl-4-styryl-2-pyrazolines and their oxidation to the corresponding pyrazoles
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The 3-benzoyl-4-styryl-2-pyrazolines 2a-g were prepared from the regioselective 1,3-dipolar cycloaddition reactions of (E,E)- cinnamylideneacetophenones 1a-g and diazomethane. The new compounds 3-(2- benzofuranyl)-4-styryl-2-pyrazolines (5c,d) were also obtained as by-products in some cases. The oxidation of the 3-benzoyl-4-styryl-2-pyrazolines 2a-g into 3(5)-benzoyl-4-styrylpyrazoles 3a-g is also reported. Configurational and conformational features of all compounds were established by NMR spectroscopy.
- Pinto, Diana C. G. A.,Silva, Artur M. S.,Levai, Albert,Cavaleiro, Jose A. S.,Patonay, Tamas,Elguero, Jose
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p. 2593 - 2599
(2007/10/03)
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- Photochemical transformations in some cyclopropyl ketones
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Irradiation of trans-1-benzoyl-2-trans-styrylcyclopropane (IIa) and trans-1-p-toluoyl-2-trans-styrylcyclopropane (IIb), leads to formation of cis disubstituted cyclopropanes (IIIa) and (IIIb) respectively.However, photolysis of trans-1-trans-cinnamoyl-2-phenylcyclopropane (IV) results in isomerzation of the α,β-double bond to produce V.Photolysis of trans-1-trans-p-methoxycinnamoyl-2-p-methoxyphenylcyclopropane (VI), by contrast, produces only a cyclobutane dimer formulated as (VII).Irradiation of 7-phenyl-3-benzylidenespirooctan-2-one (IXb), under identical conditions, leads to isomerisation around the C=C bond.The structural assignments are based, interalia, on 13C NMR and 1H NMR spectral data.
- Gandhi, R. P.,Aryan, R. C.,Ishar, M. P. S.
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p. 899 - 905
(2007/10/02)
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- The Reaction of Butadienylphosphonates with a Oxosulfonium Ylide, Phosphonium Ylides, and Ketone Enolates
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The condensation of diethyl (ethoxycarbonylmethyl)phosphonate (1a) with cinnamaldehyde in the presence of piperidine gave a 1:1 mixture of diethyl (1E,3E)- (2a) and (1Z,3E)-(1-ethoxycarbonyl-4-phenyl-1,3-butadienyl)phosphonates (2b) in 82percent yield, while a similar reaction using diethyl phosphonates (1c) exclusively gave diethyl (1E,3E)-phosphonates (4) in 78percent and 93percent yields, respectively.The reaction of the butadienylphosphonates 2-4 with dimethyloxosulfonium methylide (5) gave mixtures of (E)- and (Z)-(1-substituted 2-styrylcyclopropyl)phosphonates 7-9 in good yields.Similar treatment of the butadienylphosphonate 2 with phosphonium ylides 16a-c led to (3-substituted 1-ethoxycarbonyl-2-styrylcyclopropyl)phosphonates 17a-c in moderate yields.Reduction and oxidation of 7 were studied.The reaction of the phosphonates, 2 and 4, with ketone enolates and ketones resulted in the formation of unexpected olefins 22-24 and dienes 20a, b.The reaction mechanism is discussed.
- Minami, Toru,Yamanouchi, Takenobu,Tokumasu, Shigehumi,Hirao, Ichiro
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p. 2127 - 2131
(2007/10/02)
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